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MrtinoRG

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USPTO-ORD-100K

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Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of tert-butyl (4,6-difluoro-1-formyl-2,3-dihydro-1H-inden-1-yl)carbamate from Step F (890 mg, 2.99 mmol), methyl 1-aminocyclopentanecarboxylate (4.25 g, 29.7 mmol, described in Intermediate 25), and AcOH (2.10 mL, 36.7 mmol) in MeOH (32 mL) was stirred at ambient temperature for 20 min. NaCNBH3 (405 mg, 6.44 mmol) was added and the pH of the mixture was checked and adjusted to pH˜5 as necessary by addition of AcOH. The reaction mixture was stirred at ambient temperature for 23 h, then quenched with saturated aqueous NaHCO3 (80 mL) and extracted with EtOAc (200 mL). The organic extract was washed with H2O (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with hexane:EtOAc-100:0 to 30:70, to give the title compound. MS: m/z=425 (M+1). ### ORD JSON:

{"inputs": {"m1_m2_m3_m4_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl (4,6-difluoro-1-formyl-2,3-dihydro-1H-inden-1-yl)carbamate"}], "amount": {"mass": {"value": 890.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl 1-aminocyclopentanecarboxylate"}], "amount": {"mass": {"value": 4.25, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Intermediate 25"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "AcOH"}], "amount": {"volume": {"value": 2.1, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "MeOH"}], "amount": {"volume": {"value": 32.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "AcOH"}], "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "NaCNBH3"}], "amount": {"mass": {"value": 405.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "was stirred at ambient temperature for 20 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "The reaction mixture was stirred at ambient temperature for 23 h", "duration": {"value": 23.0, "units": "HOUR"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "quenched with saturated aqueous NaHCO3 (80 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "amount": {"volume": {"value": 80.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with EtOAc (200 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "The organic extract"}, {"type": "WASH", "details": "was washed with H2O (50 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "The crude product was purified by silica gel chromatography", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "eluting with hexane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 20.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of tert-butyl 5-(benzyloxy)-3-bromo-1H-indole-1-carboxylate (2.011 g), 1-morpholinoprop-2-en-1-one (0.776 g), palladium acetate (31 mg), tri-o-tolylphosphine (187 mg) and triethylamine (1.14 mL) in N,N-dimethylformamide (14 mL) under nitrogen atmosphere was stirred at 100° C. overnight. The mixture was diluted with ethyl acetate and saturated ammonium chloride. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (80% ethyl acetate-hexane) to give the desired product. ### ORD JSON:

{"inputs": {"m6_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m8_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl 5-(benzyloxy)-3-bromo-1H-indole-1-carboxylate"}], "amount": {"mass": {"value": 2.011, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-morpholinoprop-2-en-1-one"}], "amount": {"mass": {"value": 0.776, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tri-o-tolylphosphine"}], "amount": {"mass": {"value": 187.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 1.14, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "amount": {"volume": {"value": 14.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "palladium acetate"}], "amount": {"mass": {"value": 31.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "was stirred at 100\u00b0 C. overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "The aqueous layer was extracted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "the combined organic layers were dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated"}, {"type": "CUSTOM", "details": "The residue was purified by flash chromatography (80% ethyl acetate-hexane)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 60 ml of conc. sulfuric acid were added dropwise to a solution of 424.0 g (2 mol) of 2,4-dichloro-3-methylbenzoic acid and 1500 ml of methanol. The reaction mixture was refluxed for 5 hours, cooled, concentrated under reduced pressure and subsequently taken up in 1000 ml of methylene chloride. The organic phase was washed with water, then with 5% strength sodium bicarbonate solution and then once more with water, dried and concentrated under reduced pressure. 401.0 g of methyl 2,4-dichloro-3-methylbenzoate were obtained. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "sulfuric acid"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2,4-dichloro-3-methylbenzoic acid"}], "amount": {"mass": {"value": 424.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 1500.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The reaction mixture was refluxed for 5 hours", "duration": {"value": 5.0, "units": "HOUR"}}, {"type": "TEMPERATURE", "details": "cooled"}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "WASH", "details": "The organic phase was washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "with 5% strength sodium bicarbonate solution and then once more with water, dried", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "methyl 2,4-dichloro-3-methylbenzoate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 401.0, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of the lithocholic acid 1 (25.1 g, 66.4 mmol) in anhydrous methanol (100 mL), 4M HCl in 1,4-dioxane (100 mL) was added and the reaction mixture stirred at ambient temperature overnight. The reaction mixture became heterogeneous. The reaction mixture was diluted with dichloromethane (300 mL) and the organic layer was washed with saturated NaHCO3 (2×200 mL). The organic layer was concentrated and dried under high vacuum overnight to provide the pure ester as a white solid (25.7 g, 97%). The analytical and spectral data were consistent with that of reported values (Rensen, Patrick C. N.; van Leeuwen, Steven H.; Sliedregt, Leo A. J. M.; Van Berkel, Theo J. C.; Biessen, Erik A. L. Design and Synthesis of Novel N-Acetylgalactosamine-Terminated Glycolipids for Targeting of Lipoproteins to the Hepatic Asialoglycoprotein Receptor. Journal of Medicinal Chemistry (2004), 47(23), 5798-5808.). ### ORD JSON:

{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "lithocholic acid"}], "amount": {"mass": {"value": 25.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "1,4-dioxane"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the reaction mixture stirred at ambient temperature overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "the organic layer was washed with saturated NaHCO3 (2\u00d7200 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "The organic layer was concentrated"}, {"type": "CUSTOM", "details": "dried under high vacuum overnight", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "ester"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 25.7, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 97.0}}], "isolated_color": "white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 1.42 g (4.33 mmol) of the compound of Example 13A is reacted analogously to the synthesis of the compound of Example 20A with 1.28 g (6.50 mmol) of 3-chloro-4-fluorophenylhydrazine hydrochloride. After hydrolysis, 854 mg (59% of theory) of the title compound is obtained. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "amount": {"mass": {"value": 1.42, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "compound"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-chloro-4-fluorophenylhydrazine hydrochloride"}], "amount": {"mass": {"value": 1.28, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 0.62 g (1.07 mmol) methanesulfonic acid 4-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-5-(2-chloro-phenyl)-pyrimidin-2-ylmethyl ester in 10 ml CH2Cl2 1.53 ml (8.52 mmol) of a 5.6 M solution of dimethylamine were added. The reaction mixture was stirred for 16 hrs. at RT and than poured into H2O and extracted three times with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 200:10:1) to give 0.40 g (70%) 5-(2-chloro-phenyl)-2-dimethylaminomethyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a colorless oil, MS (ISP): 531.1 (M+H+). ### ORD JSON:

{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methanesulfonic acid 4-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-5-(2-chloro-phenyl)-pyrimidin-2-ylmethyl ester"}], "amount": {"mass": {"value": 0.62, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylamine"}], "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred for 16 hrs"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "extracted three times with 50 ml CH2Cl2", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The combined organic layers were dried (MgSO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "evaporated"}, {"type": "CUSTOM", "details": "The residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 200:10:1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CH2Cl2 MeOH NH4OH"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 16.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "5-(2-chloro-phenyl)-2-dimethylaminomethyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.4, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 70.0}}], "isolated_color": "colorless", "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: The compound of EXAMPLE 2 (7 g) and 100 ml of toluene was stirred and heated to 70°. To this mixture was added, dropwise, a solution of 14 g ammonium dimethyl phosphorodithioate in 200 ml methanol. The resulting mixture was kept at 70° for 6 hours, then the methanol was distilled off. Toluene (400 ml) was added, and the mixture was washed with water, separated, dried and evaporated under reduced pressure. The solid which remained was washed with toluene and filtered. The solid, m.p. 125°-130°, weighed 2.5 g. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "amount": {"mass": {"value": 7.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium dimethyl phosphorodithioate"}], "amount": {"mass": {"value": 14.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "heated to 70\u00b0"}, {"type": "ADDITION", "details": "To this mixture was added"}, {"type": "DISTILLATION", "details": "the methanol was distilled off", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "Toluene (400 ml) was added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Toluene"}], "amount": {"volume": {"value": 400.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "the mixture was washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "separated"}, {"type": "CUSTOM", "details": "dried"}, {"type": "CUSTOM", "details": "evaporated under reduced pressure"}, {"type": "WASH", "details": "The solid which remained was washed with toluene", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "toluene"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}], "outcomes": [{"reaction_time": {"value": 6.0, "units": "HOUR"}, "products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Twenty five grams of (3-methoxyphenyl)acetonitrile are dissolved in 200 ml of anhydrous THF in an Erlermeyer ground-necked flask. 60% sodium hydride (8.88 g; 0.37 mol) is added to the solution and the reaction mixture is heated at reflux for 30 minutes with stirring. Dimethyl carbonate (58 ml; 0.6814 mol) is then added dropwise in the course of half an hour and the reaction mixture is subsequently heated at reflux for 2 hours with stirring. The reaction mixture is poured into cold and slightly acidic water. The aqueous phase is extracted with ether, and then the ethereal phase is washed with water before being evaporated. A solution of potassium carbonate (47.15 g; 0.34 mol ) is added to the oil obtained above. After stirring, the mixture is washed with ether. The ethereal phase obtained is rewashed with a solution of potassium carbonate (12.02 g; 0.08 mol). The two aqueous phases are combined, immediately acidified, and extracted with ether. The organic phase so obtained is washed with a 10% sodium hydrogen carbonate solution, dried over magnesium sulphate and evaporated under reduced pressure to yield the title product in the form of an orangey yellow oil. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 47.15, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "(3-methoxyphenyl)acetonitrile"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "amount": {"mass": {"value": 8.88, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 12.02, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Dimethyl carbonate"}], "amount": {"volume": {"value": 58.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "with stirring"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "the reaction mixture is heated"}, {"type": "TEMPERATURE", "details": "at reflux for 30 minutes", "duration": {"value": 30.0, "units": "MINUTE"}}, {"type": "TEMPERATURE", "details": "the reaction mixture is subsequently heated"}, {"type": "TEMPERATURE", "details": "at reflux for 2 hours", "duration": {"value": 2.0, "units": "HOUR"}}, {"type": "STIRRING", "details": "with stirring"}, {"type": "EXTRACTION", "details": "The aqueous phase is extracted with ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "the ethereal phase is washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "before being evaporated"}, {"type": "CUSTOM", "details": "obtained above"}, {"type": "STIRRING", "details": "After stirring"}, {"type": "WASH", "details": "the mixture is washed with ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The ethereal phase obtained"}, {"type": "EXTRACTION", "details": "extracted with ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The organic phase so obtained"}, {"type": "WASH", "details": "is washed with a 10% sodium hydrogen carbonate solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydrogen carbonate"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over magnesium sulphate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulphate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title product"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 5 g of 2,6-diiodo-4-nitroaniline was dissolved in 20 ml of conc. sulfuric acid and cooled with ice. Sodium nitrite previously vacuum-dried was added to the solution in portions to effect the diazotization reaction at 0°-5° C. The reaction product was added dropwise to ice-water to dilute the sulfuric acid. A solution of 1.4 g of sodium azide in 10 cc of water was added dropwise to the mixture, stirred for about one hour, filtered and washed with water. After the recrystallization from ethanol followed by drying, 2,6-diiodo-4-nitroazidobenzene was obtained. ### ORD JSON:

{"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium azide"}], "amount": {"mass": {"value": 1.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "sulfuric acid"}], "reaction_role": "SOLVENT"}]}, "m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-diiodo-4-nitroaniline"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sulfuric acid"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "stirred for about one hour"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "cooled with ice"}, {"type": "DRY_WITH_MATERIAL", "details": "Sodium nitrite previously vacuum-dried", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Sodium nitrite"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "was added to the solution in portions"}, {"type": "CUSTOM", "details": "the diazotization reaction at 0\u00b0-5\u00b0 C"}, {"type": "FILTRATION", "details": "filtered"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "After the recrystallization from ethanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "by drying"}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2,6-diiodo-4-nitroazidobenzene"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 3-(5-Butylthiophen-2-yl)-5-{4-[(S)-2-fluorodecyloxy]-phenyl}-isoxazole is prepared similar to Example 6, but 3-(5-butylthiophen-2-yl)-5-(4-hydroxyphenyl)-isoxazole is etherified with (S)-2-fluoro-1-decanol by the method of Mitsunobu (diethyl azodicarboxylate/triphenylphosphine in tetrahydrofuran; Synthesis 1981, 1). ### ORD JSON:

{"inputs": {"m0_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(5-butylthiophen-2-yl)-5-(4-hydroxyphenyl)-isoxazole"}], "reaction_role": "REACTANT"}]}, "m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-2-fluoro-1-decanol"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diethyl azodicarboxylate triphenylphosphine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "3-(5-Butylthiophen-2-yl)-5-{4-[(S)-2-fluorodecyloxy]-phenyl}-isoxazole"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Into a round bottom flask was added methyl 3-(4-chlorophenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (0.28 g, 0.76 mmol) dissolved in phosphoryl chloride (3.2 mL, 34.5 mmol) and N,N-diisopropylethylamine (0.29 mL, 1.7 mmol). The reaction mixture was heated to 120° C. and stirred for 5 h. The mixture was then cooled to rt and concentrated. The residue was poured over ice and the resulting solid was filtered and washed with water to afford methyl 2-chloro-3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate (0.26 g, 98%). LC-MS: (FA) ES+ 350. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 3-(4-chlorophenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate"}], "amount": {"mass": {"value": 0.28, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "phosphoryl chloride"}], "amount": {"volume": {"value": 3.2, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N,N-diisopropylethylamine"}], "amount": {"volume": {"value": 0.29, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 120.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "stirred for 5 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The mixture was then cooled to rt", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CONCENTRATION", "details": "concentrated"}, {"type": "ADDITION", "details": "The residue was poured over ice"}, {"type": "FILTRATION", "details": "the resulting solid was filtered"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 5.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "methyl 2-chloro-3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.26, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 98.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 98.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 15.8 g of 4-chloro-4,4-difluorobutyric acid are mixed with 50 ml of thionyl chloride and 0.2 ml of dimethylformamide and heated to +70° C. over the course of 2 hours and then maintained at +70° C. for a further 30 minutes. The reaction mixture is distilled in vacuo, and the liquid boiling at 35°-37° C./21 mbar is collected. 10.5 g of 4-chloro-4,4-difluorobutyryl chloride are obtained in the form of a clear colourless liquid. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-4,4-difluorobutyric acid"}], "amount": {"mass": {"value": 15.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "thionyl chloride"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylformamide"}], "amount": {"volume": {"value": 0.2, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "heated to +70\u00b0 C. over the course of 2 hours", "duration": {"value": 2.0, "units": "HOUR"}}, {"type": "TEMPERATURE", "details": "maintained at +70\u00b0 C. for a further 30 minutes", "duration": {"value": 30.0, "units": "MINUTE"}}, {"type": "DISTILLATION", "details": "The reaction mixture is distilled in vacuo"}, {"type": "CUSTOM", "details": "the liquid boiling at 35\u00b0-37\u00b0 C./21 mbar is collected", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "liquid"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "4-chloro-4,4-difluorobutyryl chloride"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 10.5, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2,6-Difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(89 mg, 0.40 mmol), potassium carbonate (83 mg, 0.60 mmol) and 1-(bromomethyl)-2-(butyloxy)benzene (for a preparation see Intermediate 2)(114 mg, 0.47 mmol) were weighed into a vial with a stirrer. N,N-dimethylformamide (1 ml) was added, the vial was capped and the mixture was stirred at room temperature for 28 h. The reaction mixture was filtered (hydrophobic frit), washing with MeOH to give a total volume of 2 ml. This solution was purified by MDAP (Sunfire column, formic acid buffer) (Method B). The solvent was removed to give the title compound as a colourless solid (9.4 mg); LCMS: (System 4) MH+=386, tRET=3.17 min. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(bromomethyl)-2-(butyloxy)benzene"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-Difluoro-N-1H-pyrazol-3-ylbenzamide"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 9"}], "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 2"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 83.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at room temperature for 28 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the vial was capped"}, {"type": "FILTRATION", "details": "The reaction mixture was filtered (hydrophobic frit)"}, {"type": "WASH", "details": "washing with MeOH", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MeOH"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "to give a total volume of 2 ml"}, {"type": "CUSTOM", "details": "This solution was purified by MDAP (Sunfire column, formic acid buffer) (Method B)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "formic acid"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The solvent was removed"}], "outcomes": [{"reaction_time": {"value": 28.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 9.4, "units": "MILLIGRAM"}}}], "isolated_color": "colourless", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: (S)-[1-(Dimethoxyphosphinyl)-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester (100 mg; see example 1) was dissolved in 2 ml of acetonitrile, thiourea (23 mg) was added, and the mixture was refluxed under a nitrogen atmosphere for 20 hours. Solvent was then removed in vacuo and the residue was worked into a hygroscopic powder by triturating several times with anhydrous ether yielding (S)-[2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinyl]phosphonic acid, methyl ester, thiuronium salt. ### ORD JSON:

{"inputs": {"m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-[1-(Dimethoxyphosphinyl)-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "thiourea"}], "amount": {"mass": {"value": 23.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "the mixture was refluxed under a nitrogen atmosphere for 20 hours", "duration": {"value": 20.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "Solvent was then removed in vacuo"}, {"type": "CUSTOM", "details": "by triturating several times with anhydrous ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "(S)-[2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinyl]phosphonic acid, methyl ester"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "thiuronium"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A flame-dried flask is charged with N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-cinnolinecarboxamide (0.23 g, 0.52 mmol), NEt3 (0.15 mL, 1.08 mmol), Pd(PPh3)2Cl2 (0.071 g, 0.10 mmol), methanol (0.85 mL, 20.98 mmol), and anhydrous DMF (5 mL). The reaction is placed under a CO balloon atmosphere and heated at 70° C. for 5 h at which point TLC shows disappearance of starting material. The reaction is cooled to room temperature and poured into 40 mL 1N HCl. The resulting solid is filtered and dried. The crude solid is dissolved in CH2Cl2/MeOH and adsorbed onto silica. Purification by chromatography (eluent 1% MeOH/CH2Cl2 (1 L), 1.5% MeOH/CH2Cl2 (1 L), 2% MeOH/CH2Cl2 (3L), 3% MeOH/CH2Cl2 (1 L)) affords the desired product as an off-white solid (0.12 g, 0.33 mmol, 64%). Physical characteristics are as follows: m.p. 308-310° C.; 1H NMR (300 MHz, DMSO-d6) δ 14.37, 9.80, 8.72, 8.34, 7.83, 7.41, 4.55, 3.92; IR (drift) 1725, 1661, 1625, 1600, 1581, 1535, 1486, 1296, 1276, 1245, 1237, 1129, 823, 806, 761 cm−1; MS (EI) m/z 371 (M+), 142, 141, 140, 139, 125, 89, 88, 74, 73, 51; HRMS (FAB) calcd for C18H14ClN3O4+H1 372.0751, found 372.0757. ### ORD JSON:

{"inputs": {"m1_m2_m6_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-cinnolinecarboxamide"}], "amount": {"mass": {"value": 0.23, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NEt3"}], "amount": {"volume": {"value": 0.15, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 0.85, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd(PPh3)2Cl2"}], "amount": {"mass": {"value": 0.071, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m4": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 70.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The reaction is cooled to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "FILTRATION", "details": "The resulting solid is filtered"}, {"type": "CUSTOM", "details": "dried"}, {"type": "DISSOLUTION", "details": "The crude solid is dissolved in CH2Cl2/MeOH", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CH2Cl2 MeOH"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "Purification by chromatography (eluent 1% MeOH/CH2Cl2 (1 L), 1.5% MeOH/CH2Cl2 (1 L), 2% MeOH/CH2Cl2 (3L), 3% MeOH/CH2Cl2 (1 L))", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "eluent"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "MeOH CH2Cl2"}], "amount": {"volume": {"value": 1.0, "units": "LITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "MeOH CH2Cl2"}], "amount": {"volume": {"value": 1.0, "units": "LITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "MeOH CH2Cl2"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "MeOH CH2Cl2"}], "amount": {"volume": {"value": 1.0, "units": "LITER"}}, "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "AMOUNT", "amount": {"moles": {"value": 0.33, "units": "MILLIMOLE"}}}, {"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.12, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 64.0}}], "isolated_color": "off-white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Acetic acid (5R)-3-(3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester (15.2 g, 60 mM) was dissolved in a mixture of chloroform (100 ml) and acetonitrile (100 ml) under nitrogen, and silver trifluoroacetate (16.96 g, 77 mM) added. Iodine (18.07 g, 71 mM) was added in portions over 30 minutes to the vigorously stirred solution, and stirring continued at ambient temperature for 18 hours. As reaction was not complete, a further portion of silver trifluoroacetate (2.64 g, 12 mM) was added and stirring continued for 18 hours. After filtration, the mixture was added to sodium thiosulfate solution (3%, 200 ml) and dichloromethane (200 ml), and the organic phase separated, washed with sodium thiosulfate (200 ml), saturated aqueous sodium bicarbonate (200 ml), brine (200 ml), dried (magnesium sulfate), filtered and evaporated. The crude product was suspended in isohexane (100 ml), and sufficient diethyl ether added to dissolve out the brown impurity while stirring for 1 hour. Filtration gave the desired product (24.3 g) as a cream solid. ### ORD JSON:

{"inputs": {"m1_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Acetic acid (5R)-3-(3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester"}], "amount": {"mass": {"value": 15.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "silver trifluoroacetate"}], "amount": {"mass": {"value": 2.64, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Iodine"}], "amount": {"mass": {"value": 18.07, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "silver trifluoroacetate"}], "amount": {"mass": {"value": 16.96, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "stirring"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "As reaction"}, {"type": "STIRRING", "details": "stirring"}, {"type": "WAIT", "details": "continued for 18 hours", "duration": {"value": 18.0, "units": "HOUR"}}, {"type": "FILTRATION", "details": "After filtration"}, {"type": "ADDITION", "details": "the mixture was added to sodium thiosulfate solution (3%, 200 ml) and dichloromethane (200 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium thiosulfate"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the organic phase separated"}, {"type": "WASH", "details": "washed with sodium thiosulfate (200 ml), saturated aqueous sodium bicarbonate (200 ml), brine (200 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium thiosulfate"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried (magnesium sulfate)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "evaporated"}, {"type": "ADDITION", "details": "sufficient diethyl ether added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "reaction_role": "WORKUP"}]}}, {"type": "DISSOLUTION", "details": "to dissolve out the brown impurity"}, {"type": "STIRRING", "details": "while stirring for 1 hour", "duration": {"value": 1.0, "units": "HOUR"}}, {"type": "FILTRATION", "details": "Filtration"}], "outcomes": [{"reaction_time": {"value": 18.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 24.3, "units": "GRAM"}}}], "isolated_color": "cream", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2,3-dihydrobenzofuran-5-boronic acid (0.114 g, 0.693 mmol) and 3-bromoaniline (0.05 mL, 0.462 mmol) were combined in DME (2 mL) in a flame-dried, round-bottom flask. Na2CO3 (2M, 0.485 mL, 0.970 mmol) and Pd(PPh3)4 (0.017 g, 0.014 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum and the resulting residue was resuspended in H2O and extracted with CH2Cl2. The organic phase was dried over MgSO4 and concentrated under vacuum. The crude product was purified by silica column chromatography (5-20% EtOAc/hexanes). The purification was monitored by TLC. The solvent was removed under vacuum from fractions containing product, resulting in 0.0762 g in 78% yield. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "DME"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2CO3"}], "amount": {"volume": {"value": 0.485, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd(PPh3)4"}], "amount": {"mass": {"value": 0.017, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2,3-dihydrobenzofuran-5-boronic acid"}], "amount": {"mass": {"value": 0.114, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-bromoaniline"}], "amount": {"volume": {"value": 0.05, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The reaction was refluxed overnight under argon flow", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "The solvent was removed under vacuum"}, {"type": "EXTRACTION", "details": "extracted with CH2Cl2", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organic phase was dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under vacuum"}, {"type": "CUSTOM", "details": "The crude product was purified by silica column chromatography (5-20% EtOAc/hexanes)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "EtOAc hexanes"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The purification"}, {"type": "CUSTOM", "details": "The solvent was removed under vacuum from fractions"}, {"type": "ADDITION", "details": "containing product"}, {"type": "CUSTOM", "details": "resulting in 0.0762 g in 78% yield"}], "outcomes": [{"products": [{"measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 78.0}}]}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Tert-butyl (3-bromo-2-chloro-5-cyanophenyl)carbamate (834 mg, 2.52 mmol), tert-butyl 2-(dimethylcarbamoyl)piperazine-1-carboxylate (647 mg, 2.52 mmol), Pd2(dba)3 (230 mg, 0.252 mmol), BINAP (157 mg, 0.252 mmol), Cs2CO3 (1229 mg, 3.77 mmol), and toluene (20 mL) were combined in a 250 ml flask. The flask was evacuated and backfilled with N2 3×, and the reaction was heated at 105° C. for 12 h. LCMS indicated SM was still present, so an additional 0.1 eq. each of catalyst and ligand were added, and the reaction was again purged with N2 and heated at 105° C. for 13 h. An additional 0.1 eq. each of catalyst and ligand were added, and the reaction was again purged with N2 and heated at 105° C. for 2 h. The reaction was cooled to room temperature and diluted with EtOAc. The solution was filtered through celite and the filtrate concentrated in vacuo. The crude material was purified by flash column chromatography (0-50% EtOAc/Hex; 120 g column). Tert-butyl 4-(3-((tert-butoxycarbonyl)amino)-2-chloro-5-cyanophenyl)-2-(dimethylcarbamoyl)piperazine-1-carboxylate (450 mg) was obtained as an orange glass. ### ORD JSON:

{"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "catalyst"}], "reaction_role": "CATALYST"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "catalyst"}], "reaction_role": "CATALYST"}]}, "m1_m2_m7_m3_m4_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "Tert-butyl (3-bromo-2-chloro-5-cyanophenyl)carbamate"}], "amount": {"mass": {"value": 834.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tert-butyl 2-(dimethylcarbamoyl)piperazine-1-carboxylate"}], "amount": {"mass": {"value": 647.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "BINAP"}], "amount": {"mass": {"value": 157.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Cs2CO3"}], "amount": {"mass": {"value": 1229.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd2(dba)3"}], "amount": {"mass": {"value": 230.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 105.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The flask was evacuated"}, {"type": "CUSTOM", "details": "the reaction was again purged with N2", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "N2"}], "reaction_role": "WORKUP"}]}}, {"type": "TEMPERATURE", "details": "heated at 105\u00b0 C. for 13 h", "duration": {"value": 13.0, "units": "HOUR"}, "temperature": {"setpoint": {"value": 105.0, "units": "CELSIUS"}}}, {"type": "CUSTOM", "details": "the reaction was again purged with N2", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "N2"}], "reaction_role": "WORKUP"}]}}, {"type": "TEMPERATURE", "details": "heated at 105\u00b0 C. for 2 h", "duration": {"value": 2.0, "units": "HOUR"}, "temperature": {"setpoint": {"value": 105.0, "units": "CELSIUS"}}}, {"type": "TEMPERATURE", "details": "The reaction was cooled to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "ADDITION", "details": "diluted with EtOAc", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "The solution was filtered through celite"}, {"type": "CONCENTRATION", "details": "the filtrate concentrated in vacuo"}, {"type": "CUSTOM", "details": "The crude material was purified by flash column chromatography (0-50% EtOAc/Hex; 120 g column)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude material"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "Tert-butyl 4-(3-((tert-butoxycarbonyl)amino)-2-chloro-5-cyanophenyl)-2-(dimethylcarbamoyl)piperazine-1-carboxylate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 450.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: prepared by reaction of 5-(4-chloro-phenyl)-2-methyl-thiazole-4-carboxylic acid with (R)-6-methyl-imidazo[2,1-b]-thiazole-5-carboxylic acid-piperidin-3-ylamide. ### ORD JSON:

{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(4-chloro-phenyl)-2-methyl-thiazole-4-carboxylic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(R)-6-methyl-imidazo[2,1-b]-thiazole-5-carboxylic acid-piperidin-3-ylamide"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of benzyl N-methyl-(S)-pyrrolidin-3-ylcarbamate (Intermediate 129, 1.28 g), iodoethane (0.853 g), and potassium carbonate (1.51 g) in acetonitrile (12 mL) was stirred at room temperature for 4 hours. The mixture was evaporated in vacuo and the residue was basified with 5M sodium hydroxide and filtered through a phase separator. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-30% to give benzyl N—((S)-1-ethylpyrrolidin-3-yl)-N-methylcarbamate (0.686 g) as a colourless oil. ### ORD JSON:

{"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "benzyl N-methyl-(S)-pyrrolidin-3-ylcarbamate"}], "amount": {"mass": {"value": 1.28, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Intermediate 129"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "iodoethane"}], "amount": {"mass": {"value": 0.853, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 1.51, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "amount": {"volume": {"value": 12.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "was stirred at room temperature for 4 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The mixture was evaporated in vacuo"}, {"type": "FILTRATION", "details": "filtered through a phase separator"}, {"type": "CONCENTRATION", "details": "The filtrate was concentrated in vacuo"}, {"type": "CUSTOM", "details": "the residue was purified by chromatography on silica"}, {"type": "WASH", "details": "eluting with a mixture of methanol and DCM with a gradient of 0-30%", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 4.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "benzyl N\u2014((S)-1-ethylpyrrolidin-3-yl)-N-methylcarbamate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.686, "units": "GRAM"}}}], "isolated_color": "colourless", "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2,4,6-Trimethylbenzoic acid (mesitoic acid) (10 g, 61 mmol) was suspended in 150 mL of water, and the mixture cooled to 0° C. Sodium hydroxide pellets (7.31 g, 0.18 mol) were gradually added, followed by addition of potassium permanganate (4×7.2 g, 0.18 mol) at four intervals of 30 minutes. The mixture was stirred at room temperature for 2 hours, then heated on a steam bath for 15-30 minutes. Sulfuric acid (200 mL, 9 mol) was added, then sodium bisulfite was carefully and gradually added at 0° C. The precipitated white solid was filtered and then dissolved in 5 N ammonium hydroxide. The solution was washed with diethyl ether, then gradually treated dropwise with concentrated sulfuric acid to precipitate the product. Filtration, followed by washing with hot water (4×) and petroleum ether (3×), recrystallization (methanol-water), and drying at high vacuum gave 10.5 g (89%) of the product as a white solid, m.p. >300° C. (ref. W. A. Noyes, Amer. Chem. J., 20, 789 (1898)). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Sulfuric acid"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2,4,6-Trimethylbenzoic acid"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Sodium hydroxide"}], "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bisulfite"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium permanganate"}], "amount": {"mass": {"value": 7.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The mixture was stirred at room temperature for 2 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "were gradually added"}, {"type": "TEMPERATURE", "details": "heated on a steam bath for 15-30 minutes", "duration": {"value": 22.5, "precision": 7.5, "units": "MINUTE"}}, {"type": "ADDITION", "details": "gradually added at 0\u00b0 C", "temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}}, {"type": "FILTRATION", "details": "The precipitated white solid was filtered"}, {"type": "DISSOLUTION", "details": "dissolved in 5 N ammonium hydroxide", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium hydroxide"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The solution was washed with diethyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "gradually treated dropwise with concentrated sulfuric acid", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sulfuric acid"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "to precipitate the product"}, {"type": "FILTRATION", "details": "Filtration"}, {"type": "WASH", "details": "by washing with hot water (4\u00d7) and petroleum ether (3\u00d7), recrystallization (methanol-water)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "petroleum ether"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "methanol water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "drying at high vacuum"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 10.5, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 89.0}}], "isolated_color": "white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of 1-tert-butyl 3-methyl 4-oxopyrrolidine-1,3-dicarboxylate (48.65 g, 0.20 mol), allyl alcohol (300 mL), and dibutyltin oxide (5.0 g, 20 mmol) in anhydrous toluene (800 mL) was refluxed for 20 h under a Dean-Stark trap with portionwise removal of solvent (total of 200 mL) over the first 6 hours, followed by addition of more allyl alcohol (75 mL) at the end of the first 6 hours. The reaction mixture was concentrated, dissolved in minimal methylene chloride, and loaded onto a silica gel column (700 mL volume) and eluted with methylene chloride, 10%, then 15%, then 20% ethyl acetate/methylene chloride to afford 3-allyl 1-tert-butyl 4-oxopyrrolidine-1,3-dicarboxylate (48.6 g, 90%) as a pale pink oil (NMR and MS as above). This compound (48.47 g, 0.18 mol) was dissolved in anhydrous tetrahydrofuran (200 mL) and added to a stirred solution of Pd(PPh3)4 (4.16 g, 3.6 mmol) in anhydrous tetrahydrofuran (400 mL) under nitrogen, stirred for 4 h, and concentrated. The residue was dissolved in heptane and loaded onto a silica gel column (1000 mL volume) and eluted with 60:35:5 heptane/methylene chloride/ethyl acetate to afford tert-butyl 3-allyl-4-oxopyrrolidine-1-carboxylate (27.93, 69%) as a pale yellow oil (NMR and MS as above). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "allyl alcohol"}], "amount": {"volume": {"value": 75.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1-tert-butyl 3-methyl 4-oxopyrrolidine-1,3-dicarboxylate"}], "amount": {"mass": {"value": 48.65, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "allyl alcohol"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dibutyltin oxide"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 800.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The reaction mixture was concentrated"}, {"type": "DISSOLUTION", "details": "dissolved in minimal methylene chloride", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "eluted with methylene chloride, 10%", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "3-allyl 1-tert-butyl 4-oxopyrrolidine-1,3-dicarboxylate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 48.6, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 90.0}}], "isolated_color": "pale pink", "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: According to the procedure of Preparation 9 (a), except substituting 5-fluoro-1H-indole-3-carboxaldehyde (0.41 g, 2.5 mmole) for the ethylindole-2-carboxylate, the title compound (0.20 g, 57%) was prepared as a viscous oil: MS (ES) m/e 191 (M+H)+. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "( a )"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-fluoro-1H-indole-3-carboxaldehyde"}], "amount": {"mass": {"value": 0.41, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ethylindole-2-carboxylate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.2, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 57.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: By using 1-nitro-2-naphthyl trifluoromethanesulfonate (5.94 g, 18.5 mmol), and tert-butyl(3-aminophenyl)carbamate, the title compound (1.02 g, yield 17%) was obtained as brown crystals in the same manner as that of Example 1, (1), (2) and (3). ### ORD JSON:

{"inputs": {"m0_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "( 2 )"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "( 3 )"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-nitro-2-naphthyl trifluoromethanesulfonate"}], "amount": {"mass": {"value": 5.94, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl(3-aminophenyl)carbamate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.02, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 17.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of Example 1E (200.0 mg, 0.556 mmol), tert-butyl 4-aminobenzoate (129 mg, 0.667 mmol), and concentrated HCl (0.08 mL, 2.63 mmol) was heated at 160° C. for 30 minutes in a Biotage microwave reactor. The solvent was decanted. The remaining residue was treated with water, sonicated, filtered, washed with water, and oven-dried to provide the title compound as an HCl salt. ### ORD JSON:

{"inputs": {"m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "mixture"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tert-butyl 4-aminobenzoate"}], "amount": {"mass": {"value": 129.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 0.08, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The solvent was decanted"}, {"type": "ADDITION", "details": "The remaining residue was treated with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "sonicated"}, {"type": "FILTRATION", "details": "filtered"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "oven-dried"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To N-Boc-piperazine (500 mg) in DCM (10 ml) was added triethylamine (450 μl) and 4-fluorobenzenesulfonyl chloride (564 mg). The reaction mixture was stirred at room temperature overnight, then partitioned between dichloromethane and water, washed with brine, organics were dried over MgSO4, filtered and volatiles removed in vacuo to give 4-(4-fluoro-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (937 mg). ### ORD JSON:

{"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-Boc-piperazine"}], "amount": {"mass": {"value": 500.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 450.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-fluorobenzenesulfonyl chloride"}], "amount": {"mass": {"value": 564.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at room temperature overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "partitioned between dichloromethane and water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "organics were dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "volatiles removed in vacuo"}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "4-(4-fluoro-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 937.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A 13.6 g (0.1 mol) portion of o-methylbenzoic acid, 10.9 g (0.1 mol) of m-methoxyaniline and 10.1 g (0.1 mol) of triethylamine were dissolved in 250 ml of toluene. A 4.6 g (0.033 mol) amount of phosphorus trichloride was added dropwise to the above solution with stirring at 20°-60°C. After the addition, the reaction mixture was stirred at 80°-90°C for 3 hours. The reaction mixture was cooled and washed with water to remove the triethylamine hydrochloride, and the product was dried over anhydrous sodium sulfate. The toluene was removed to give 22.8 g (95%) of fine white prismatic crystals having a melting point of 142°-143°C. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "phosphorus trichloride"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "o-methylbenzoic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "m-methoxyaniline"}], "amount": {"mass": {"value": 10.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"mass": {"value": 10.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "with stirring at 20\u00b0-60\u00b0C"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "After the addition"}, {"type": "STIRRING", "details": "the reaction mixture was stirred at 80\u00b0-90\u00b0C for 3 hours", "duration": {"value": 3.0, "units": "HOUR"}}, {"type": "TEMPERATURE", "details": "The reaction mixture was cooled"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "to remove the triethylamine hydrochloride", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylamine hydrochloride"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "the product was dried over anhydrous sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The toluene was removed", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "toluene"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "fine white prismatic crystals"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 22.8, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 95.0}}], "isolated_color": "fine white prismatic", "texture": {"type": "CRYSTAL", "details": "crystals"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: In like manner, but using dimethyl aspartate and dimethyl glutamate in place of diethyl malonate affords the corresponding N-[3β-hydroxy-11-oxo-18β-olean-12-en-30-oyl]aspartic acid and glutamic acid compounds which are converted to their disodium salts according to Example I-C. ### ORD JSON:

{"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "dimethyl aspartate"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "dimethyl glutamate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "N-[3\u03b2-hydroxy-11-oxo-18\u03b2-olean-12-en-30-oyl]aspartic acid"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "glutamic acid"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of ((1R,3S)-2,2-dimethyl-3-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)cyclobutyl)carbamate (438 mg, 1.14 mmol) and palladium on activated carbon (10% Pd, 50 mg) in MeOH (15 mL) was stirred at 25° C. under hydrogen atmosphere for 5 h. The reaction mixture was filtered through celite and the filtrate was concentrated to afford the crude title compound (340 mg, crude). MS (ESI) m/z 251.2[M+H]+. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "((1R,3S)-2,2-dimethyl-3-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)cyclobutyl)carbamate"}], "amount": {"mass": {"value": 438.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "palladium on activated carbon"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}, {"identifiers": [{"type": "NAME", "value": "MeOH"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 25.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "was stirred at 25\u00b0 C. under hydrogen atmosphere for 5 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "The reaction mixture was filtered through celite"}, {"type": "CONCENTRATION", "details": "the filtrate was concentrated"}], "outcomes": [{"reaction_time": {"value": 5.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "crude title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 340.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of methyl {4-chloro-6-(dimethylamino)-2-[4-(methylamino)benzyl]pyrimidin-5-yl}acetate (0.080 g, 0.23 mmol), 1-hydroxybenzotriazole (0.043 g, 0.32 mmol), triethylamine (0.11 mL, 0.80 mmol), and 4-chlorobenzoic acid (0.043 g, 0.28 mmol) was treated with WSCI (0.066 g, 0.34 mmol) at room temperature and the reaction mixture was stirred at room temperature for 16 hours. EtOAc was then added and the organic layer was washed sequentially with 0.5N HCl, saturated NaHCO3, and brine, dried over anhydrous Na2SO4, filtered, and concentrated to dryness to give the crude product methyl[4-chloro-2-{4-[(4-chlorobenzoyl)(methyl)amino]benzyl}-6-(dimethylamino)pyrimidin-5-yl]acetate. ### ORD JSON:

{"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "SOLVENT"}]}, "m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl {4-chloro-6-(dimethylamino)-2-[4-(methylamino)benzyl]pyrimidin-5-yl}acetate"}], "amount": {"mass": {"value": 0.08, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-hydroxybenzotriazole"}], "amount": {"mass": {"value": 0.043, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 0.11, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-chlorobenzoic acid"}], "amount": {"mass": {"value": 0.043, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the reaction mixture was stirred at room temperature for 16 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "the organic layer was washed sequentially with 0.5N HCl, saturated NaHCO3, and brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated to dryness"}], "outcomes": [{"reaction_time": {"value": 16.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "methyl[4-chloro-2-{4-[(4-chlorobenzoyl)(methyl)amino]benzyl}-6-(dimethylamino)pyrimidin-5-yl]acetate"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: (Method E-3) 2-(3-Bromo-phenylamino)-4-chlorobenzoic acid, 14 (4 g, 12.2 mmol) was heated in conc. H2SO4 (50 ml) for 30 min then allowed to cool to room temperature. Water was added slowly and the precipitate filtered off, washed with water and dried over phosphorous pentoxide. The crude material was suspended in DMF (50 mL) and added under nitrogen to NaH (1.2 g, 50 mmol) in DMF (50 mL). After 30 min dimethylsulphate (3 ml, 18 mmol) was added and stirring continued for 1 hr. Addition of water gave a precipitate the title compound (625 mg, 2.02 mmol, 17%) as the more polar product after separation by column chromatography (ethyl acetate:hexane 1:4) ### ORD JSON:

{"inputs": {"m4_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "NaH"}], "amount": {"mass": {"value": 1.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m1_m2_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(3-Bromo-phenylamino)-4-chlorobenzoic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "14"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "H2SO4"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "dimethylsulphate"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "stirring"}, "conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "the precipitate filtered off"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over phosphorous pentoxide", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "phosphorous pentoxide"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "AMOUNT", "amount": {"moles": {"value": 2.02, "units": "MILLIMOLE"}}}, {"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 625.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 17.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of the product of Example 11A (1.2 g, 3.1 mmol) in tetrahydrofuran (400 mL) was added hydrazine hydrate (550 mg, 9.4 mmol) and the mixture was stirred at ambient temperature for 12 hours. After concentration, the residue was washed with methanol and dried under vacuum to give the title compound, which was used in the next step without further purification. MS: 379 (M+H+). ### ORD JSON:

{"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 1.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrazine hydrate"}], "amount": {"mass": {"value": 550.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 400.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at ambient temperature for 12 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "After concentration"}, {"type": "WASH", "details": "the residue was washed with methanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried under vacuum"}], "outcomes": [{"reaction_time": {"value": 12.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2-iodo-2-phenylethanol was synthesized as described in Golumbic, C. and Cottle, D. L. J. Am. Chem. Soc. 61, 996 (1939). An aqueous HI solution (81.7 grams, 54.7%) and 556 ml of water were added to a 1 L reaction flask equipped with an addition funnel, which was cooled to zero degrees C. Styrene oxide (40 grams) and 50 grams of ethanol were added to the addition funnel. The styrene oxide solution was added dropwise to the flask over a 40-minute period during which a white precipitate was formed. Filtration over a fritted glass funnel followed by drying under vacuum for four hours yielded 69.8 grams of a white solid having a melting point of 62-66° C. The solid was dissolved in 560 ml of ethanol and poured into rapidly stirred water (2.5 L containing 100 ml of 5% NaHSO3). The white precipitate was collected on a fritted glass funnel and dried in a vacuum oven at room temperature for four hours in the presence of P2O5 as a desiccant. The white solid (24 grams) had a melting point of 75.5-76° C. NMR analysis was consistent with the reports in the above-cited literature. ### ORD JSON:

{"inputs": {"m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "HI"}], "amount": {"mass": {"value": 81.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 556.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "Styrene oxide"}], "amount": {"mass": {"value": 40.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"mass": {"value": 50.0, "units": "GRAM"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "styrene oxide"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "equipped with an addition funnel"}, {"type": "CUSTOM", "details": "was formed"}, {"type": "FILTRATION", "details": "Filtration over a fritted glass funnel"}, {"type": "CUSTOM", "details": "by drying under vacuum for four hours", "duration": {"value": 4.0, "units": "HOUR"}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "2-iodo-2-phenylethanol"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "white solid"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 69.8, "units": "GRAM"}}}], "isolated_color": "white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: The title compound was prepared by a procedure similar to that described for D4 starting from 3,4,5-trifluorobenzaldehyde (1.0 g, 6.25 mmol),)4-chloro-3-fluorophenol. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "D4"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3,4,5-trifluorobenzaldehyde"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-3-fluorophenol"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 5-nitro-oxindole (25 g) in 120 mL of dimethylacetamide in a Parr bottle was added 10% Pd/C (0.5 g). The mixture was hydrogenated (40 psi H2) for 16 h. The catalyst was removed by filtration and the filtrate was diluted with ether (2 L) to provide 5-amino-oxindole (10.5 g; 50%). ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5-nitro-oxindole"}], "amount": {"mass": {"value": 25.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylacetamide"}], "amount": {"volume": {"value": 120.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "Pd/C"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "for 16 h", "duration": {"value": 16.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "The catalyst was removed by filtration"}, {"type": "ADDITION", "details": "the filtrate was diluted with ether (2 L)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "amount": {"volume": {"value": 2.0, "units": "LITER"}}, "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "5-amino-oxindole"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 10.5, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 50.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 50.5}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: The title compound is prepared by reacting 4-cyano-4-phenylpiperidine with 1-(2-bromoethyl)phthalimide to obtain 1-[2-(4-cyano-4-phenylpiperidin-1-yl)ethyl]phthalimide and reacting it with hydrazine. ### ORD JSON:

{"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-cyano-4-phenylpiperidine"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(2-bromoethyl)phthalimide"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "1-[2-(4-cyano-4-phenylpiperidin-1-yl)ethyl]phthalimide"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of 25.1 g (0.1 mole) of 5-acetamido 4,7-dimethoxy 6-piperidinoethoxy benzofuran were brought to reflux for 10 hours in 200 ml of 2 N hydrochloric acid. Then it was neutralized with concentrated soda, extracted with ethyl acetate, the solvent was evaporated, the residue was taken up again in acetone and 30 ml of 7 N hydrochloric ethanol were added. It was filtered and recrystallized in ethanol. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-acetamido 4,7-dimethoxy 6-piperidinoethoxy benzofuran"}], "amount": {"mass": {"value": 25.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "with concentrated soda"}, {"type": "EXTRACTION", "details": "extracted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the solvent was evaporated"}, {"type": "ADDITION", "details": "30 ml of 7 N hydrochloric ethanol were added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "It was filtered"}, {"type": "CUSTOM", "details": "recrystallized in ethanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Methyl 4-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-bromobenzoate (4.12 g, 9.9 mmol) was added to a solution of LiBH4 (429 mg, 19.8 mmol) in THF/ether/H2O (20/20/1 mL) and was allowed to stir at 25° C. After 16 hours, the reaction was quenched with H2O (10 mL). The reaction mixture was diluted with dichloromethane (25 mL) and was extracted with 1N HCl (30 mL×3) and brine (30 mL). The organic extracts were dried over Na2SO4 and evaporated. The crude product was purified by chromatography on silica gel (eluting with 0-100% ethyl acetate in hexanes) to afford 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamide (2.84 g, 74%). ESI-MS m/z calc. 389.0. found 390.1 (M+1)+; retention time 2.91 minutes. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Methyl 4-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-bromobenzoate"}], "amount": {"mass": {"value": 4.12, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "LiBH4"}], "amount": {"mass": {"value": 429.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF ether H2O"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 25.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "to stir at 25\u00b0 C"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the reaction was quenched with H2O (10 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "The reaction mixture was diluted with dichloromethane (25 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "was extracted with 1N HCl (30 mL\u00d73) and brine (30 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organic extracts were dried over Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated"}, {"type": "CUSTOM", "details": "The crude product was purified by chromatography on silica gel (eluting with 0-100% ethyl acetate in hexanes)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hexanes"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 16.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamide"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.84, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 74.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one (93.4 g, 401 mmol) in 2.6 L of acetone was added 400 mL of Jone's reagent (2.45 M) at 0° C. The reaction was warmed to room temperature, and the mixture was stirred overnight. The solid was removed by filtration, and the filtrate was concentrated. The concentrated residue was poured into water. The resulting white solid was collected and washed with water and dried to obtain 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid. 1H NMR δ (400 MHz, d6-DMSO): 8.34 (s, 1H), 7.42-7.33 (m, 5H), 6.91(s, 1H), 4.95 (s, 2H). ### ORD JSON:

{"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one"}], "amount": {"mass": {"value": 93.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "reagent"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetone"}], "amount": {"volume": {"value": 2.6, "units": "LITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The solid was removed by filtration"}, {"type": "CONCENTRATION", "details": "the filtrate was concentrated"}, {"type": "ADDITION", "details": "The concentrated residue was poured into water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The resulting white solid was collected"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 54 g of 2',4'-dichloro-2-(3-pyridyl)-acetophenone are added portionwise under an inert gas to a suspension of 46.5 g of freshly sublimed potassium tert.butylate in 590 ml of tert.butanol and the reaction mixture is stirred at 45° C. for 2 hours. The mixture is treated at room temperature with 59.5 g of 2-chloroethyl-dimethylsulphonium iodide and a spatula tip of sodium iodide and the mixture is held at 50° C. for 16 hours while stirring vigorously. The mixture is poured into water and extracted three times with 300 ml of diethyl ether each time. The combined organic extracts are washed with water, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The residue is chromatographed on silica gel with diethyl ether as the eluent and crystallized from diethyl ether/n-hexane. There are obtained 41.7 g of 2,4-dichlorophenyl 1-(3-pyridyl)-cyclopropyl ketone as white crystals, m.p. 83° C. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium iodide"}], "reaction_role": "REACTANT"}]}, "m1_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "2',4'-dichloro-2-(3-pyridyl)-acetophenone"}], "amount": {"mass": {"value": 54.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium tert.butylate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tert.butanol"}], "amount": {"volume": {"value": 590.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloroethyl-dimethylsulphonium iodide"}], "amount": {"mass": {"value": 59.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 45.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the reaction mixture is stirred at 45\u00b0 C. for 2 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "while stirring vigorously"}, {"type": "EXTRACTION", "details": "extracted three times with 300 ml of diethyl ether each time", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined organic extracts are washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous sodium sulphate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulphate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue is chromatographed on silica gel with diethyl ether as the eluent", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "crystallized from diethyl ether/n-hexane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether n-hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2,4-dichlorophenyl 1-(3-pyridyl)-cyclopropyl ketone"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 41.7, "units": "GRAM"}}}], "isolated_color": "white", "texture": {"type": "CRYSTAL", "details": "crystals"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a mixture of 17.0 g (4.31×10-2 mol) of 3,5-dicarbomethoxyphenyldiphenylphosphine oxide (from Preparation 3), 4.71 g (4.65×10-2 mol) of triethylamine and 196 ml of dry toluene under nitrogen was added 6.76 g (4.74×10-2 mol) of trichlorosilane. The mixture was then heated at reflux for 15.25 hr and cooled. A solution of 20% sodium hydroxide (49 ml) was added and the mixture was stirred. The organic layer was separated, washed with two 250 ml portions of water, dried over MgSO4 and concentrated to an oil which crystallized. The solid was recrystallized twice from methanol and dried. The yield of 3,5-dicarbomethoxyphenyldiphenylphosphine was 14.0 g (85.8% of theory); mp=103°-4.5° C. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 49.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3,5-dicarbomethoxyphenyldiphenylphosphine oxide"}], "amount": {"mass": {"value": 17.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"mass": {"value": 4.71, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 196.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "trichlorosilane"}], "amount": {"mass": {"value": 6.76, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "the mixture was stirred"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The mixture was then heated"}, {"type": "TEMPERATURE", "details": "at reflux for 15.25 hr", "duration": {"value": 15.25, "units": "HOUR"}}, {"type": "TEMPERATURE", "details": "cooled"}, {"type": "CUSTOM", "details": "The organic layer was separated"}, {"type": "WASH", "details": "washed with two 250 ml portions of water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "two"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated to an oil which"}, {"type": "CUSTOM", "details": "crystallized"}, {"type": "CUSTOM", "details": "The solid was recrystallized twice from methanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "3,5-Dicarbomethoxyphenyldiphenylphosphine"}]}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 1-(1,1′-biphenyl-4-ylthio)propan-2-one (69 mg, 0.28 mmol) was stirred at room temperature with sodium bicarbonate (72 mg, 0.85 mmol), oxone ((525 mg, 0.85 mmol), water (5 ml) and methanol (10 ml) for 3 hours. Water (50 ml) was added and the product extracted into ethyl acetate (3×25 ml). The extracts were brine washed, sodium sulphate dried and evaporated to give 78 mg (99%) product that was of sufficient purity to use with out further purification. ### ORD JSON:

{"inputs": {"m1_m2_m3_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(1,1\u2032-biphenyl-4-ylthio)propan-2-one"}], "amount": {"mass": {"value": 69.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "amount": {"mass": {"value": 72.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "oxone"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "the product extracted into ethyl acetate (3\u00d725 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed"}, {"type": "DRY_WITH_MATERIAL", "details": "sodium sulphate dried", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulphate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 78.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 99.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of tert-butyl 2-hydroxyethylcarbamate (25 mL, 161.6 mmol) in dichloromethane (60 mL) was cooled to 0° C. and stirred while first diisopropylethylamine (33.8 mL, 193.9 mmol) was added and then mesyl chloride (13.7 mL, 177.8 mmol) then was added dropwise. The mixture was allowed to warm to 23° C., stirred for 18 hours, poured into dichloromethane (200 mL) and washed with aqueous hydrochloric acid (3M, 3×25 mL) and saturated aqueous sodium hydrogencarbonate (2×25 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo to provide tert-butyl 2-methylsulfonyloxyethylcarbamate (37.39 g, 97% yield) as a brown oil; MS (PB-PCI) C8H17NO5S m/e calc 239.08; found 240 (MH+). ### ORD JSON:

{"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl 2-hydroxyethylcarbamate"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "diisopropylethylamine"}], "amount": {"volume": {"value": 33.8, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "mesyl chloride"}], "amount": {"volume": {"value": 13.7, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 23.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "stirred for 18 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "was added"}, {"type": "WASH", "details": "washed with aqueous hydrochloric acid (3M, 3\u00d725 mL) and saturated aqueous sodium hydrogencarbonate (2\u00d725 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium hydrogencarbonate"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The organic layer was separated"}, {"type": "DRY_WITH_MATERIAL", "details": "dried (MgSO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}], "outcomes": [{"reaction_time": {"value": 18.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "tert-butyl 2-methylsulfonyloxyethylcarbamate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 37.39, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 97.0}}], "isolated_color": "brown", "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2-Amino-5-trifluoromethylphenol was prepared by treating 2-nitro-5-trifluoromethylphenol (500 mg, 2.41 mmol) with a solution of SnCl2 (3.5 g, mmol) in EtOH at 23° C. for 12 h. The mixture was concentrated to 50 mL and adjusted to pH7 using saturated sodium bicarbonate. The reaction mixture was partitioned between H2O and EtOAc. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting colorless oil(370 mg, 87%) was used without further purification. 1H NMR (CDCl3): 7.6 (s, 1H), 7.39(d, 1H, J=8.5 Hz), 7.08(d, 1H, J=8.5 Hz) ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-nitro-5-trifluoromethylphenol"}], "amount": {"mass": {"value": 500.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "SnCl2"}], "amount": {"mass": {"value": 3.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "EtOH"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The mixture was concentrated to 50 mL"}, {"type": "CUSTOM", "details": "The reaction mixture was partitioned between H2O and EtOAc", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The aqueous layer was separated"}, {"type": "EXTRACTION", "details": "extracted with EtOAc", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The combined organic extracts were dried over sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "The resulting colorless oil(370 mg, 87%) was used without further purification", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "oil"}], "amount": {"mass": {"value": 370.0, "units": "MILLIGRAM"}}, "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "2-Amino-5-trifluoromethylphenol"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: In analogy to the procedure described in example 7 a], (6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester (example 5 b]) was reacted with 5-chloromethyl-2-(4-trifluoromethoxy-phenyl)-pyridine in the presence of cesium carbonate and potassium iodide, using acetonitrile as solvent, to obtain the title compound as colorless crystals. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester"}], "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "reaction_role": "SOLVENT"}]}, "m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "5-chloromethyl-2-(4-trifluoromethoxy-phenyl)-pyridine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "cesium carbonate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium iodide"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "isolated_color": "colorless", "texture": {"type": "CRYSTAL", "details": "crystals"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of EXAMPLE 167B (3.13 g) in dioxane/water (3:1, 40 mL) was added 2,6-lutidine (2.5 mL), OsO4 (2.5% in tert-butanol, 2.75 mL), and NaIO4 (8.55 g) under argon. The reaction mixture was stirred at room temperature for 4 hours, then water (50 mL) and dichloromethane (200 mL) were added. The organic layer was separated, and the water phase was extracted by dichloromethane (3×200 mL). The combined organic layers were washed with brine (200 mL) and dried over Na2SO4. After filtration, the solvent was removed to give the crude product which was used in the next step without further purification. ### ORD JSON:

{"inputs": {"m1_m6_m2_m7_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "amount": {"mass": {"value": 3.13, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2,6-lutidine"}], "amount": {"volume": {"value": 2.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaIO4"}], "amount": {"mass": {"value": 8.55, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dioxane water"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "OsO4"}], "amount": {"volume": {"value": 2.75, "units": "MILLILITER"}}, "reaction_role": "CATALYST"}]}, "m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at room temperature for 4 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The organic layer was separated"}, {"type": "EXTRACTION", "details": "the water phase was extracted by dichloromethane (3\u00d7200 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined organic layers were washed with brine (200 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "After filtration"}, {"type": "CUSTOM", "details": "the solvent was removed"}], "outcomes": [{"reaction_time": {"value": 4.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of 100 mg (0.26 mmol) of 5-chloro-N-[1,3-dioxo-2-(4-piperidinyl)-2,3-dihydro-1H-isoindol-4-yl]-2-thiophenecarboxamide, 0.022 ml (0.31 mmol) of α-bromoacetonitrile and 0.072 ml (0.51 mmol) of triethylamine in 2.5 ml of DMF are stirred at room temperature overnight. The mixture is concentrated and the residue is taken up in dichloromethane, washed with sodium bicarbonate solution, dried over magnesium sulfate and concentrated. The product is crystallized with ether, filtered off with suction and dried under high vacuum. Alternatively, the product can be purified by chromatography on silica gel (dichloromethane/methanol mixtures). ### ORD JSON:

{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "5-chloro-N-[1,3-dioxo-2-(4-piperidinyl)-2,3-dihydro-1H-isoindol-4-yl]-2-thiophenecarboxamide"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "\u03b1-bromoacetonitrile"}], "amount": {"volume": {"value": 0.022, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 0.072, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 2.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "are stirred at room temperature overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The mixture is concentrated"}, {"type": "WASH", "details": "washed with sodium bicarbonate solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated"}, {"type": "CUSTOM", "details": "The product is crystallized with ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered off with suction"}, {"type": "CUSTOM", "details": "dried under high vacuum"}, {"type": "CUSTOM", "details": "Alternatively, the product can be purified by chromatography on silica gel (dichloromethane/methanol mixtures)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane methanol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 1.44 g (1.25 mmol)Pd(PPh3)4 was added under argon at room temperature to a solution of 6-bromo-pyridine-3-carbaldehyde in 60 ml 1,2 dimethoxyethane and stirred for 15 min. 63 ml (125 mmol) of 2 M sodium carbonate solution and 2.5 g (13.16 mmol) of 3-(trifluoromethyl-)-phenylboronic acid were added and the mixture heated to boiling temperature for 18 hours (h). The reaction mixture was cooled to room temperature, filtered, and the filtrate evaporated. The residue was taken up with ethyl acetate, washed twice with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.18 g (36%) of 6-(3-Trifluoromethyl-phenyl)-pyridine-3-carbaldehyde ### ORD JSON:

{"inputs": {"m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium carbonate"}], "amount": {"volume": {"value": 63.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-(trifluoromethyl-)-phenylboronic acid"}], "amount": {"mass": {"value": 2.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m5_m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "6-bromo-pyridine-3-carbaldehyde"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1,2 dimethoxyethane"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "Pd(PPh3)4"}], "amount": {"mass": {"value": 1.44, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "stirred for 15 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "the mixture heated"}, {"type": "CUSTOM", "details": "for 18 hours", "duration": {"value": 18.0, "units": "HOUR"}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "the filtrate evaporated"}, {"type": "WASH", "details": "washed twice with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over sodium sulphate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulphate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated"}], "outcomes": [{"reaction_time": {"value": 15.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "6-(3-Trifluoromethyl-phenyl)-pyridine-3-carbaldehyde"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.18, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 36.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 30 g of 2,6-dibromoanthraquinone, 5 g of Zn and 25 g of NaOH were stirred in 200 mL of water at 100° C. for 24 hours and when the reaction was complete, the reaction materials were filtered. The thus-obtained organic material and inorganic material were dissolved in chloroform and the resulting mixture was re-filtered. The obtained filtrate was applied to a silica gel short column, thereby separating the inorganic material. The separated material was recrystallized from MC and MeOH, thereby obtaining 15 g of 2,6-dibromoanthracene. ### ORD JSON:

{"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-dibromoanthraquinone"}], "amount": {"mass": {"value": 30.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaOH"}], "amount": {"mass": {"value": 25.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "Zn"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "the reaction materials were filtered"}, {"type": "DISSOLUTION", "details": "The thus-obtained organic material and inorganic material were dissolved in chloroform", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "the resulting mixture was re-filtered"}, {"type": "CUSTOM", "details": "separating the inorganic material"}, {"type": "CUSTOM", "details": "The separated material was recrystallized from MC and MeOH", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MeOH"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "2,6-dibromoanthracene"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 15.0, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture potassium tert-butoxide (1.1 g, 9.6 mmol) and diethyl malonate (3.8 g, 24 mmol) in THF (25 ml) and HMPA (8 ml) was stirred at room temperature under argon atmosphere for 1 hr. To this solution the triflate (8) (1.47 g, 2.4 mmol) in THF (20 ml) was added and the mixture was stirred at room temperature for 26 hr. The usual work-up (ether for extraction) gave a crude product, which was applied to a column of silica gel (100 g). Elution with n-hexane-ether (5:1) provided the diester (9) (1.20 g, 81%), mp 79°-80° C. (ethanol). IR γmaxKBr cm-1 : 1750, 1740. 1H-NMR δ: 0.73 (3H, s, 18-H3), 1.00 (3H, s, 19-H3), 1.10 (3H, d, J=6 Hz, 21-H3), 1.27 (6 H, t, J=7 Hz, --CO2CH2CH3), 3.46 (2H, m, THP), 3.62 (1H, t, J=6 Hz, 25-H), 3.80 (1H, m, 3-H), 4.14 (4H, q, J=JHz, --COCH2CH3), 4.64 (1H, m, THP), 5.30 (1H, m, 6-H). MS m/z: 538 (M+-DHP), 520, 505. ### ORD JSON:

{"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "triflate"}], "amount": {"mass": {"value": 1.47, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium tert-butoxide"}], "amount": {"mass": {"value": 1.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diethyl malonate"}], "amount": {"mass": {"value": 3.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HMPA"}], "amount": {"volume": {"value": 8.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at room temperature for 26 hr"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "The usual work-up (ether for extraction)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "gave a crude product, which", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "Elution with n-hexane-ether (5:1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "n-hexane-ether"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 26.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "diester"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.2, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 81.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of N-cyano-3-trifluoromethylaniline (5.0 g) in acetone (100 ml) , potassium carbonate (7.4 g) and propargyl bromide (3.5 g) were added, and the resultant mixture was stirred at room temperature for 10 hours, followed by filtration of the reaction mixture. The solvent was removed from the filtrate by distillation under reduced pressure, and the residue was subjected to column chromatography to give N-cyano-N-propargyl-3-trifluoromethylaniline (3.8 g). The thus obtained N-cyano-N-propargyl-3-trifluoromethylaniline (1 g) and a catalytic amount of triethylamine were dissolved in methanol (30 ml), and the resultant mixture was cooled to 0° C. Hydrogen sulfide was gradually introduced into the mixture for 20 minutes while keeping the temperature at 0° C., followed by introduction of nitrogen gas to remove hydrogen sulfide. The solvent was removed by distillation, and the residue was subjected to column chromatography to give 0.2 g of 2-imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine (Compound (ix)). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Hydrogen sulfide"}], "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "N-cyano-N-propargyl-3-trifluoromethylaniline"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant mixture"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "at 0\u00b0 C.", "temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}}, {"type": "CUSTOM", "details": "to remove hydrogen sulfide", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrogen sulfide"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The solvent was removed by distillation"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "2-imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.2, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: In a glass tube with screw-on lid, 2 g (7.43 mmol) of 4-bromo-2,6-dichloro-N,N-dimethylaniline (known from European Journal of Organic Chemistry (2006), (19), 4398-4404) are initially charged with 86 mg (0.14 mmol) of xantphos and 136 mg (0.14 mmol) of tris(dibenzylideneacetone)-dipalladium in 10 ml of DMF. 1.01 g (8.92 mmol) of trimethylsilylacetonitrile and 0.46 g (4.46 mmol) of zinc fluoride are then added, and in the closed vessel the reaction is heated at 90° C. for 16 hours. The reaction mixture is cooled, water and ethyl acetate are added and the mixture is filtered through silica gel. ### ORD JSON:

{"inputs": {"m4_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m6_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-bromo-2,6-dichloro-N,N-dimethylaniline"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "xantphos"}], "amount": {"mass": {"value": 86.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "tris(dibenzylideneacetone)-dipalladium"}], "amount": {"mass": {"value": 136.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}, "m3_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "trimethylsilylacetonitrile"}], "amount": {"mass": {"value": 1.01, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "zinc fluoride"}], "amount": {"mass": {"value": 0.46, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 90.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The reaction mixture is cooled"}, {"type": "FILTRATION", "details": "the mixture is filtered through silica gel"}], "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Allyl bromide (3.6 g, 30.09 mmol) and triethyl phosphite (1 g, 6 mmol) were dissolved and reacted in chloroform (30 mL). Then, the resulting reaction solution was refluxed for 12 hours, cooled to room temperature and filtered through a glass filter. Chloroform was completely removed from the solution under vacuum to thereby give an oily compound as the title compound. The 1H NMR and 13CNMR results of the compound thus obtained are given as follows. ### ORD JSON:

{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Allyl bromide"}], "amount": {"mass": {"value": 3.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethyl phosphite"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Then, the resulting reaction solution"}, {"type": "TEMPERATURE", "details": "was refluxed for 12 hours", "duration": {"value": 12.0, "units": "HOUR"}}, {"type": "FILTRATION", "details": "filtered through a glass"}, {"type": "FILTRATION", "details": "filter"}, {"type": "CUSTOM", "details": "Chloroform was completely removed from the solution under vacuum", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Chloroform"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: (R)-tert-Butyl 6-bromo-4-fluoro-2,3-dihydro-1H-inden-1-ylcarbamate (1.1 g, 3.33 mol, 1.0 eq.) was dissolved in MeOH (35 ml) and DMSO (30 ml), and the mixture was degassed for 30 minutes with argon. Pd(OAc)2 (0.038 g, 0.166 mmol, 0.05 eq.), 1,3-bis(diphenylphosphino)-propane (0.068 g, 0.166 mmol, 0.05 eq.) and TEA (1.39 ml, 9.99 mmol, 3.0 eq.) were then added, and stirring was carried out for 16 hours in a pressure vessel at 75° C. under CO pressure (80 psi). The reaction mixture was concentrated, diluted with water (50 ml) and extracted with ethyl acetate (2×75 ml). The combined org. phases were washed with sat. NaCl solution (60 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 10% ethyl acetate in hexane). Yield: 83% (0.86 g, 2.783 mmol) ### ORD JSON:

{"inputs": {"m5_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1,3-bis(diphenylphosphino)-propane"}], "amount": {"mass": {"value": 0.068, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "TEA"}], "amount": {"volume": {"value": 1.39, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd(OAc)2"}], "amount": {"mass": {"value": 0.038, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-tert-Butyl 6-bromo-4-fluoro-2,3-dihydro-1H-inden-1-ylcarbamate"}], "amount": {"mass": {"value": 1.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "MeOH"}], "amount": {"volume": {"value": 35.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "stirring"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "DMSO (30 ml), and the mixture was degassed for 30 minutes with argon", "duration": {"value": 30.0, "units": "MINUTE"}, "input": {"components": [{"identifiers": [{"type": "NAME", "value": "DMSO"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "The reaction mixture was concentrated"}, {"type": "ADDITION", "details": "diluted with water (50 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with ethyl acetate (2\u00d775 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 75.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "phases were washed with sat. NaCl solution (60 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaCl"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "purified by column chromatography (silica gel, 10% ethyl acetate in hexane)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 16.0, "units": "HOUR"}, "products": [{"measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 83.0}}]}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Under a nitrogen atmosphere, 3,5-dimethylphenol (40.9 mmoles) was dissolved in 40 mL water and 40 mL ether. To this was added 1.5 equivalents (61.4 mmoles) of sodium nitrate (NaNO3). The reaction was cooled in an ice bath and 50 mL concentrated HCl was slowly added to the reaction. The reaction was warmed to room temperature and followed by TLC (ethyl acetate:hexanes, 1:1) until the reaction was complete (0.5 hour). The reaction was extracted into ether (×3), washed with saturated NaHCO3, saturated NaCl, dried over MgSO4, filtered, rinsed with ether, and concentrated. The product was purified using silica-gel chromatography, yielding 3,5-dimethyl-4-nitro-phenol as a yellow solid (2.05 grams; 30% yield). The product was characterized by NMR (DMSO). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "hexanes"}], "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium nitrate"}], "amount": {"moles": {"value": 61.4, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3,5-dimethylphenol"}], "amount": {"moles": {"value": 40.9, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The reaction was cooled in an ice bath"}, {"type": "CUSTOM", "details": "(0.5 hour)", "duration": {"value": 0.5, "units": "HOUR"}}, {"type": "EXTRACTION", "details": "The reaction was extracted into ether (\u00d73)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with saturated NaHCO3, saturated NaCl", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "NaCl"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "WASH", "details": "rinsed with ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated"}, {"type": "CUSTOM", "details": "The product was purified"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "3,5-dimethyl-4-nitro-phenol"}], "measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 30.0}}], "isolated_color": "yellow", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Dissolve benzo[b]thiophen-6-ol (10 g, 67 mmol) in pyridine (300 mL). Add 2,2-dimethyl-propionyl chloride (38 mL, 308 mmol) dropwise, and stir at room temperature for 8 hours. Concentrate in vacuo to ¼ Volume, partition between ethyl acetate (250 mL) and water (250 mL). Separate layers, wash organic layer with water (250 mL) and brine (200 mL). Dry with magnesium sulfate, filter, and concentrate in vacuo to give 15 g of 2,2-dimethyl-propionic acid benzo[b]thiophen-6-yl ester (98%). ### ORD JSON:

{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "benzo[b]thiophen-6-ol"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2,2-dimethyl-propionyl chloride"}], "amount": {"volume": {"value": 38.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "Concentrate in vacuo"}, {"type": "CUSTOM", "details": "partition between ethyl acetate (250 mL) and water (250 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "Separate layers, wash organic layer with water (250 mL) and brine (200 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "Dry with magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filter"}, {"type": "CONCENTRATION", "details": "concentrate in vacuo"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "2,2-dimethyl-propionic acid benzo[b]thiophen-6-yl ester"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 15.0, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 98.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 10 millimoles (1.17 g) of benzyl cyanide are dissolved in 0 ml of anhydrous toluene at 0° C., under an argon atmosphere. 15 millimoles of 1.5M toluenic solution of diisobutylaluminum hydride (10 ml) are added, dropwise, at this temperature. The temperature is maintained at 0° C. for one hour, then 13.7 ml (viz 1.5 eq) of diethyl-aluminum cyanide are added. The reaction mixture is stirred for 3 hours while the temperature reaches the room temperature. Then it is hydrolyzed with 10 ml of methanol, and with a slurry of sodium sulfate. After purification of the so-obtained α-aminonitrile, by high pressure liquid chromatrography on silica, with elution by ethyl acetate/petroleum ether, there are obtained 0.95 g of 2-amino -3-phenyl-propionitrile, in the form of an orange-colored oil, yield: 65%. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl-aluminum cyanide"}], "amount": {"volume": {"value": 13.7, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "toluenic solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diisobutylaluminum hydride"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "benzyl cyanide"}], "amount": {"mass": {"value": 1.17, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture is stirred for 3 hours while the temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "After purification of the so-obtained \u03b1-aminonitrile", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "\u03b1-aminonitrile"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "by high pressure liquid chromatrography on silica, with elution by ethyl acetate/petroleum ether, there", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate petroleum ether"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 3.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2-amino -3-phenyl-propionitrile"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.95, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 65.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A sealed tube containing a solution of 4-(4-chloro-7H-pyrrolo[2,3-d]-pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (250 mg, 0.75 mmol), 1-naphthylamine (160 mg, 1.12 mmol) and trifluoroacetic acid (287 μL, 3.73 mmol) in 2,2,2-trifluoroethanol (5 mL) was heated at 80° C. and maintained at this temperature overnight. The product was poured into saturated NaHCO3 solution (50 mL) and the precipitate was filtered off, giving the title compound as an off-white solid. 1H NMR (DMSO-d6, 400 MHz): δ=9.48 (1H, s), 8.14-7.92 (3H, m), 7.82 (1H, d, J=8.0 Hz), 7.64 (1H, d, J=7.2 Hz), 7.61-7.44 (3H, m), 6.40 (1H, s), 4.02 (2H, brs), 3.51 (2H, brs), 2.89 (2H, brs); MS (ES+): m/z 342.11 [MH+], HPLC: tR=1.71 min (MicromassZQ, polar—5 min). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(4-chloro-7H-pyrrolo[2,3-d]-pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester"}], "amount": {"mass": {"value": 250.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-naphthylamine"}], "amount": {"mass": {"value": 160.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "trifluoroacetic acid"}], "amount": {"volume": {"value": 287.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2,2,2-trifluoroethanol"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 80.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "maintained at this temperature overnight", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}, {"type": "FILTRATION", "details": "the precipitate was filtered off"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "isolated_color": "off-white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 10.5 g (54.7 mmol, 1 eq.) 1-(2-oxo-ethyl)-cyclopropanecarboxylic acid tert-butyl ester and 13.21 g (1.08 eq.) N-benzylglycine tert-butyl ester were dissolved in 140 ml toluene. 21 g (1.63 eq.) sodium triacetoxyborohydride were added (exotherm from 25° C. to 28° C.) and the reaction mixture was stirred 5 h at RT (IPC by GC). A solution of 2 ml (0.64 eq.) AcOH in 15 ml toluene was added. After 30 min at RT, the reaction mixture was cooled to 0° C. and 100 ml sat. aq. NaHCO3 solution was added over 40 min (foaming). 50 ml EtOAc were added. The mixture was stirred for 30 min at RT. The mixture was extracted with 200 ml and a second time with 50 ml EtOAc. The organic phases were washed with 50 ml sat. aq. NaHCO3 solution followed by 50 ml sat. aq. NaCl solution. The organic phases were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 21.5 g of the title compound as an oil (ca. 95% yield, corrected for ca 3% residual toluene and 3% amine starting material). ### ORD JSON:

{"inputs": {"m8": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(2-oxo-ethyl)-cyclopropanecarboxylic acid tert-butyl ester"}], "amount": {"mass": {"value": 10.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-benzylglycine tert-butyl ester"}], "amount": {"mass": {"value": 13.21, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 140.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m4_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "AcOH"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium triacetoxyborohydride"}], "amount": {"mass": {"value": 21.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the reaction mixture was stirred 5 h at RT (IPC by GC)"}, "conditions_are_dynamic": true}, "workups": [{"type": "WAIT", "details": "After 30 min at RT", "duration": {"value": 30.0, "units": "MINUTE"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "TEMPERATURE", "details": "the reaction mixture was cooled to 0\u00b0 C.", "temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}}, {"type": "STIRRING", "details": "The mixture was stirred for 30 min at RT", "duration": {"value": 30.0, "units": "MINUTE"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "EXTRACTION", "details": "The mixture was extracted with 200 ml"}, {"type": "WASH", "details": "The organic phases were washed with 50 ml sat. aq. NaHCO3 solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}], "outcomes": [{"reaction_time": {"value": 5.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 21.5, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 95.0}}], "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a stirred solution of N-(4-methyl-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamide (330 mg, 1.11 mmol) in a mixture of EtOH (25 mL) and water (2.5 mL) was added ammonium chloride (300 mg, 5.55 mmol) and iron powder (250 mg, 4.44 mmol). The reaction mixture was heated at 100° C. for 2 hr before being cooled, filtered through Celite® and concentrated under reduced pressure. The residue was partitioned between water (20 mL) and DCM (40 mL) and the organic layer was separated, washed with brine (20 mL), passed through a phase separation cartridge and concentrated under reduced pressure to give N-(1-(4-amino-1-methyl-1H-pyrazol-5-yl)-4-methylazepan-4-yl)acetamide as a brown solid which was used without further purification. Following the procedure for Example 149 using this intermediate and 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)-thiazole-4-carboxylic acid gave 378 as an off-white foam (54 mg, 19% over three steps). 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 7.86 (s, 1H), 7.39-7.29 (m, 1H), 7.07-6.99 (m, 2H), 6.15 (s, 2H), 5.38 (s, 1H), 3.74 (s, 3H), 3.30-3.18 (m, 4H), 3.12 (ddd, J=13.6, 6.6, 3.1 Hz, 1H), 2.30-2.19 (m, 2H), 2.00-1.72 (m, 6H), 1.45 (s, 3H). LCMS (ES+) m/z 504 (M+1) ### ORD JSON:

{"inputs": {"m1_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(4-methyl-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamide"}], "amount": {"mass": {"value": 330.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "EtOH"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 2.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "iron"}], "amount": {"mass": {"value": 250.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "before being cooled"}, {"type": "FILTRATION", "details": "filtered through Celite\u00ae"}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was partitioned between water (20 mL) and DCM (40 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the organic layer was separated"}, {"type": "WASH", "details": "washed with brine (20 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "passed through a phase separation cartridge"}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "N-(1-(4-amino-1-methyl-1H-pyrazol-5-yl)-4-methylazepan-4-yl)acetamide"}], "isolated_color": "brown", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 200 mg of 2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-β-ethyloxime and 90 mg of triethylamine in 3 ml of dichloromethane, 169 mg of 2-(trifluoromethyl)benzoyl chloride was added dropwise with stirring under cooling with ice, and after the addition, the mixture was stirred at room temperature for another 30 minutes. After completion of the reaction, the reaction mixture was mixed with 10 ml of water and extracted with ethyl acetate (15 ml×1), the resulting organic layer was washed with water (10 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 190 mg of the desired product as a pale yellow resinous substance. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-\u03b2-ethyloxime"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"mass": {"value": 90.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-(trifluoromethyl)benzoyl chloride"}], "amount": {"mass": {"value": 169.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "with stirring"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "under cooling with ice"}, {"type": "ADDITION", "details": "after the addition"}, {"type": "STIRRING", "details": "the mixture was stirred at room temperature for another 30 minutes", "duration": {"value": 30.0, "units": "MINUTE"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "After completion of the reaction"}, {"type": "EXTRACTION", "details": "extracted with ethyl acetate (15 ml\u00d71)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "the resulting organic layer was washed with water (10 ml\u00d71)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over saturated aqueous sodium chloride", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The resulting residue was purified by silica gel column chromatography"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 190.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of 4-(2-(Pyridin-4-yl)-1H-benzo[d]imidazol-5-yl)benzene-1,2-diamine (intermediate A) (50 mg, 0.17 mmol), thieno[2,3-b]pyridine-2-carbaldehyde (33 mg, 0.20 mmol) and Na2S2O5 (38 mg. 0.20 mmol) in IPA-H2O (3:1, 8 mL) was heated under microwave radiation for 170° C. for 10 min. The mixture was absorbed onto silica and purified by column chromatography eluting with (95:5 EtOAc-MeOH to 85:15 EtOAc-MeOH) afforded the title compound as a yellow solid (30 mg, 0.07 mmol, 40%). ### ORD JSON:

{"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(2-(Pyridin-4-yl)-1H-benzo[d]imidazol-5-yl)benzene-1,2-diamine"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "intermediate A"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "thieno[2,3-b]pyridine-2-carbaldehyde"}], "amount": {"mass": {"value": 33.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Na2S2O5"}], "amount": {"mass": {"value": 38.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "IPA H2O"}], "amount": {"volume": {"value": 8.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 170.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The mixture was absorbed onto silica"}, {"type": "CUSTOM", "details": "purified by column chromatography"}, {"type": "WASH", "details": "eluting with (95:5 EtOAc-MeOH to 85:15 EtOAc-MeOH)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc MeOH"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "EtOAc MeOH"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "AMOUNT", "amount": {"moles": {"value": 0.07, "units": "MILLIMOLE"}}}, {"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 30.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 40.0}}], "isolated_color": "yellow", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Step 5 To a solution of {(R)-1-[4-Chloro-3-(3-cyano-4-methoxy-benzoyl)-2-fluoro-phenyl]-propyl}-carbamic acid tert-butyl ester (59 mg, 0.13 mmol) in DCM (2 mL) was added 4M HCl in dioxane (0.17 mL, 0.66 mmol, 5 eq.) and the reaction mixture was stirred for 60 hours. The mixture was partitioned between DCM (10 mL) and water (10 mL) made basic with 5M NaOH. The aqueous phase was extracted with further DCM (10 mL) and then the combined organics were dried (MgSO4), filtered and concentrated to give 5-[3-((R)-1-amino-propyl)-6-chloro-2-fluoro-benzoyl]-2-methoxy-benzonitrile (41 mg, 0.12 mmol) as a viscous gum. ### ORD JSON:

{"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "{(R)-1-[4-Chloro-3-(3-cyano-4-methoxy-benzoyl)-2-fluoro-phenyl]-propyl}-carbamic acid tert-butyl ester"}], "amount": {"mass": {"value": 59.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dioxane"}], "amount": {"volume": {"value": 0.17, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "the reaction mixture was stirred for 60 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The mixture was partitioned between DCM (10 mL) and water (10 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "The aqueous phase was extracted with further DCM (10 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "the combined organics were dried (MgSO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated"}], "outcomes": [{"reaction_time": {"value": 60.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "5-[3-((R)-1-amino-propyl)-6-chloro-2-fluoro-benzoyl]-2-methoxy-benzonitrile"}], "measurements": [{"type": "AMOUNT", "details": "AMOUNT", "amount": {"moles": {"value": 0.12, "units": "MILLIMOLE"}}}, {"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 41.0, "units": "MILLIGRAM"}}}], "isolated_color": "viscous", "texture": {"type": "CUSTOM", "details": "gum"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 4-methylisophthalic acid was synthesized from 2,5-dimethylbenzoic acid following a similar procedure to that described for 5-fluoroisophthalic acid. ### ORD JSON:

{"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-fluoroisophthalic acid"}], "reaction_role": "REACTANT"}]}, "m0_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2,5-dimethylbenzoic acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "4-methylisophthalic acid"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 5.0 g (13.1 mmol) of (4S)-6-iodo-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole in 250 ml of acetonitrile was added 3.5 g (37 mmol) of 2-hydroxypyridine, 16.9 g (122 mmol) of powdered potassium carbonate, and 0.30 g (0.26 mmol) of tetrakis(triphenylphosphine)palladium. The resultant mixture was heated at 65° C. under a carbon monoxide atmosphere for 14 hours. The cooled mixture was then treated with 2 ml of hydrazine hydrate and stirred for another 15 hours. After filtering, the mixture was concentrated in vacuo to provide a residue. This residue was taken up in methylene chloride and extracted with aqueous tartaric acid solution. The aqueous layer was basified with 1M sodium hydroxide solution and the product was extracted into methylene chloride. Evaporation of solvent in vacuo left an oily solid which, after thorough washing with a 1:2 mixture of toluene and hexane, afforded 0.60 g of (4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6-carboxylic hydrazide. m.p. 199°-201° C. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant mixture"}], "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "reaction_role": "SOLVENT"}]}, "m1_m6_m2_m3_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "(4S)-6-iodo-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-hydroxypyridine"}], "amount": {"mass": {"value": 3.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 16.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "tetrakis(triphenylphosphine)palladium"}], "amount": {"mass": {"value": 0.3, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrazine hydrate"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "stirred for another 15 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "After filtering"}, {"type": "CONCENTRATION", "details": "the mixture was concentrated in vacuo"}, {"type": "CUSTOM", "details": "to provide a residue"}, {"type": "EXTRACTION", "details": "extracted with aqueous tartaric acid solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "tartaric acid"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "the product was extracted into methylene chloride", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "Evaporation of solvent in vacuo"}, {"type": "WAIT", "details": "left an oily solid which"}, {"type": "WASH", "details": "after thorough washing with a 1:2 mixture of toluene and hexane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "toluene"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 15.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "(4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6-carboxylic hydrazide"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.6, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Bromine (4.25 g, 26.6 mmol) was slowly added dropwise to a solution of 1-[3-(trifluoromethyl)phenyl]ethanone (5.00 g, 26.6 mmol) in diethyl ether (100 ml), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was distilled off under reduced pressure to give the desired product as an oil quantitatively. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Bromine"}], "amount": {"mass": {"value": 4.25, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-[3-(trifluoromethyl)phenyl]ethanone"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at room temperature for 4 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "DISTILLATION", "details": "The reaction mixture was distilled off under reduced pressure"}], "outcomes": [{"reaction_time": {"value": 4.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Benzyl thiocyanate (29.8 g, 0.2 mol), chloroform (76 g, 0.6 mol) and triethylbenzylammonium chloride (0.5 g, 0.002 mol) were stirred vigorously. 40 ml of 50% aqueous sodium hydroxide were added clowly to this solution (mildly exothermic). The temperature increased to 40° C. and was maintained thereat for 4 h with efficient stirring. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Benzyl thiocyanate"}], "amount": {"mass": {"value": 29.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"mass": {"value": 76.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylbenzylammonium chloride"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 40.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "was maintained"}], "outcomes": [{"reaction_time": {"value": 4.0, "units": "HOUR"}, "products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of freshly prepared 5-Chlorocarbonyl-2-methyl-2H-1,2,3-triazole-4-carboxylic acid methyl ester (2.7 g; ca. 13 mmol) in THF (270 ml) was added ethyl-diisopropyl-amine (1.88 g; 1.1 eq.). The mixture was hydrogenated in the presence of 2.7 g 10% Pd/C at 0-5° C. at normal pressure for 2½ hours and subsequently filtered from the catalyst. The clear solution was evaporated to give the crude as a solid which was dissolved again in ethyl acetate and stirred for a couple of minutes with silica gel. After filtration and evaporation 1.77 g (84%) of pure product as off-white crystals were obtained [m.p. 107-108° C.; 1H-NMR (300 MHz, CDCl3), δ (ppm): 10.43 (s, 1H), 4.33 (s, 3H), 4.01 (s, 3H)]. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-Chlorocarbonyl-2-methyl-2H-1,2,3-triazole-4-carboxylic acid methyl ester"}], "amount": {"mass": {"value": 2.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl-diisopropyl-amine"}], "amount": {"mass": {"value": 1.88, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 270.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Pd/C"}], "amount": {"mass": {"value": 2.7, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "stirred for a couple of minutes with silica gel"}, "conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "subsequently filtered from the catalyst"}, {"type": "CUSTOM", "details": "The clear solution was evaporated"}, {"type": "CUSTOM", "details": "to give the crude as a solid which"}, {"type": "FILTRATION", "details": "After filtration"}, {"type": "CUSTOM", "details": "evaporation 1.77 g (84%) of pure product as off-white crystals", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "pure product"}], "amount": {"mass": {"value": 1.77, "units": "GRAM"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "were obtained [m.p. 107-108\u00b0 C.; 1H-NMR (300 MHz, CDCl3), \u03b4 (ppm): 10.43 (s, 1H), 4.33 (s, 3H), 4.01 (s, 3H)]"}], "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 0.78 g (1.71 mmol, 1 eq.) of freshly prepared (4-vinylbenzyl)-bis(2,4,6-trimethylbenzoyl)-phosphine (example 1) and 1.8 mL (1.6 g, 15.4 mmol, 9 eq.) styrene are dissolved in 0.6 mL toluene. 47.6 mg (2% w/w) AIBN are added and the solution is stirred at 60° C. for 50 hours. 5 ml Toluene are subsequently added to the yellow gel which is formed in order to dissolve the polymer. The polymer is then precipitated by the addition of petroleum ether. This procedure is repeated twice before the polymer is filtrated off and washed with petroleum ether. The polymer is dried under vacuum providing 2.121 g of the (4-vinylbenzyl)-bis(2,4,6-trimethylbenzoyl)-phosphine/styrene co-polymer. Conversion: 87.4%. ### ORD JSON:

{"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(4-vinylbenzyl)-bis(2,4,6-trimethylbenzoyl)-phosphine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "styrene"}], "amount": {"volume": {"value": 1.8, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 0.6, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Toluene"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "AIBN"}], "amount": {"mass": {"value": 47.6, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 60.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the solution is stirred at 60\u00b0 C. for 50 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "is formed in order"}, {"type": "DISSOLUTION", "details": "to dissolve the polymer"}, {"type": "CUSTOM", "details": "The polymer is then precipitated by the addition of petroleum ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "petroleum ether"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "is filtrated off"}, {"type": "WASH", "details": "washed with petroleum ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "petroleum ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The polymer is dried under vacuum"}], "outcomes": [{"reaction_time": {"value": 50.0, "units": "HOUR"}, "products": [{"measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.121, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2-[4-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]-N-methyl-isobutyramide was reacted with 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine in General Procedure A. Purification on silica yielded 171. (400 MHz CDCl3): 1.21 (6H, s, ar), 2.56 (8H, b, CH2), 2.80 (3H, d(J=5.03), CH3), 3.82 (2H, s, ar), 3.87-3.89 (4H, m, CH2), 4.01-4.04 (4H, m, CH2), 4.61 (1H, s, NH), 6.56 (1H, d(J=8.40), ar), 7.15 (1H, d, ar), 8.45-8.47 (1H, m, ar), 9.15 (1H, s, ar). MH+ 511.52 ### ORD JSON:

{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[4-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]-N-methyl-isobutyramide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Purification on silica"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "171"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethyl-5-oxopyrrolidin-1-yl]-2-chloro-3-methylbenzonitrile (134.5 mg) in tetrahydrofuran (10 mL)-methanol (5 mL) was added 6 mol/L hydrochloric acid (5 mL), and the mixture was stirred at room temperature for 18 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1→1/4) to give the title compound as a colorless solid (yield: 66.2 mg, 69%). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydrogen carbonate"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethyl-5-oxopyrrolidin-1-yl]-2-chloro-3-methylbenzonitrile"}], "amount": {"mass": {"value": 134.5, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at room temperature for 18 hr"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "the mixture was extracted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The extract was dried over anhydrous magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1\u21921/4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane ethyl acetate"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 18.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 66.2, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 69.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 69.4}}], "isolated_color": "colorless", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2.512 g (9.2 mmol) 3-chlorosulfonyl-4-fluorobenzoic acid was added to 2.27 mL (27.6 mmol) propylamine following the general procedure in for 2-chloro-5-[(ethylamino)sulfonyl]-4-fluorobenzoic acid. Crude product was used in subsequent step without further purification. 1H NMR (300 MHz, DMSO-d6) δ8.19-8.22 (d, 1H, J=7.84 Hz), 8.12-8.16 (t, 1H, J=11.59 Hz), 7.85-7.88 (d, 1H, J=9.90 Hz), 2.80-2.87 (q, 2H, J=6.82), 1.33-1.45 (m, 2H), 0.77-0.82 (t, 3H, J=7.51 Hz). ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-chlorosulfonyl-4-fluorobenzoic acid"}], "amount": {"mass": {"value": 2.512, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "propylamine"}], "amount": {"volume": {"value": 2.27, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-chloro-5-[(ethylamino)sulfonyl]-4-fluorobenzoic acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Crude product was used in subsequent step without further purification"}], "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Reactions similar to those of Reference Example 29 and Example 38 were performed except for using 2-chloro-5-{[(3R)-1-methylpyrrolidin-3-yl]oxy}pyrimidine, which was prepared by a method similar to that of Reference Example 30, instead of 2-chloro-5-[(1-methylpiperidin-4-yl)oxy]pyrimidine, and from 100 mg (0.155 mmol) of (−)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(piperidin-4-yl)-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 10, 58 mg of the title compound was obtained as a white solid (yield: 44%). ### ORD JSON:

{"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-5-{[(3R)-1-methylpyrrolidin-3-yl]oxy}pyrimidine"}], "reaction_role": "REACTANT"}]}, "m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-5-[(1-methylpiperidin-4-yl)oxy]pyrimidine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(\u2212)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(piperidin-4-yl)-5,6,7,8-tetrahydroquinoline"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "was prepared by a method similar to that of Reference Example 30"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 58.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "solid"}], "measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 44.0}}], "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene (13.25 g, 36.0 mmol) and NBS (6.41 g, 36.0 mmol) were combined in carbon tetrachloride (150 mL) with a catalytic amount of AIBN (0.296 g, 1.800 mmol) and stirred at reflux for 16 h. The reaction mixture was washed with water, dried over MgSO4, filtered and concentrated to dryness. The residue was purified by chromatography on 330 g silica gel eluted with 0 to 10% Et2O in hexanes to give the desired product, 2-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene (10.04 g, 22.47 mmol, 62.4% yield), as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.53-7.67 (m, 3H), 6.78 (s, 1H), 4.75 (s, 2H). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "AIBN"}], "amount": {"mass": {"value": 0.296, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene"}], "amount": {"mass": {"value": 13.25, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "NBS"}], "amount": {"mass": {"value": 6.41, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "carbon tetrachloride"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "stirred"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "at reflux for 16 h", "duration": {"value": 16.0, "units": "HOUR"}}, {"type": "WASH", "details": "The reaction mixture was washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated to dryness"}, {"type": "CUSTOM", "details": "The residue was purified by chromatography on 330 g silica gel"}, {"type": "WASH", "details": "eluted with 0 to 10% Et2O in hexanes", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Et2O"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hexanes"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "2-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene"}], "measurements": [{"type": "AMOUNT", "details": "AMOUNT", "amount": {"moles": {"value": 22.47, "units": "MILLIMOLE"}}}, {"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 10.04, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 62.4}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 62.4}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of N-triphenylmethyl-4-(trans-2-hydroxymethyl-cyclopropyl)imidazole (100 mg, 0.26 mmol) and trifluoroacetic acid (TFA) (10 mL) was stirred at room temperature for 1-3 hours. The TFA was evaporated under reduced pressure. The resulting mixture was diluted with distilled water (5 mL) and extracted with ether (3×15 mL). The aqueous layer was lyophilized to give the product (61 mg, 93% yield). ### ORD JSON:

{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-triphenylmethyl-4-(trans-2-hydroxymethyl-cyclopropyl)imidazole"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "trifluoroacetic acid"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "was stirred at room temperature for 1-3 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The TFA was evaporated under reduced pressure", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "TFA"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "The resulting mixture was diluted with distilled water (5 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with ether (3\u00d715 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 2.0, "precision": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 61.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 93.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of methyl 6-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-1-(2,4-dimethoxybenzyl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylate (1.7 g, 2.8 mmol) in THF (40 mL) was added a solution of TBAF (2.9 mL, 1M, 2.9 mmol). The dark red solution was stirred for 1 h at room temperature and then concentrated. The crude residue was purified on silica gel eluting with EtOAc to afford the title compound as yellow oil (1.3 g, 93%). ### ORD JSON:

{"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 6-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-1-(2,4-dimethoxybenzyl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylate"}], "amount": {"mass": {"value": 1.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "TBAF"}], "amount": {"volume": {"value": 2.9, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The dark red solution was stirred for 1 h at room temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "concentrated"}, {"type": "CUSTOM", "details": "The crude residue was purified on silica gel eluting with EtOAc", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude residue"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.3, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 93.0}}], "isolated_color": "yellow", "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: N2,N4-Bis(3-aminophenyl)-5-fluoro-2,4-pyrimidinediamine and tert-butyl bromoacetate were reacted together to give N2,N4-bis(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 29.34 min.; purity: 97.2%; MS (m/e): 427.07 (MH+). ### ORD JSON:

{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N2,N4-Bis(3-aminophenyl)-5-fluoro-2,4-pyrimidinediamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tert-butyl bromoacetate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "N2,N4-bis(3-tert-butoxycarbonylmethyleneaminophenyl)-5-fluoro-2,4-pyrimidinediamine"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2-Diacetylamino-4-(3-nitrophenyl)-4H-naphtho[1,2-b]pyran-3-carbonitrile (3.62 g) was dissolved in chloroform (200 ml) and mechanically stirred in the presence of Grade III alumina (36 g) for 24 hours at ambient temperature. The suspension was filtered, the alumina pad was washed through with 5% methanol in chloroform, the combined filtrates were evaporated and the residue was triturated with a little chloroform. The white solid was dissolved in dioxan (50 ml) and left to stand for 24 hours. An impurity precipitated out and this was filtered off. Water was added (200 ml) to the filtrate and the solid produced was filtered off, washed with water and dried. This solid was passed through a chloroform--`flash` silica column. The fractions containing product were bulked, evaporated to dryness and triturated with methanol to give yellow crystals of 2-acetamido-4-(3-nitrophenyl)-4H-naphtho[1,2-b]pyran-3-carbonitrile, m.p. 234.5°-236° C. ### ORD JSON:

{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Diacetylamino-4-(3-nitrophenyl)-4H-naphtho[1,2-b]pyran-3-carbonitrile"}], "amount": {"mass": {"value": 3.62, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "III"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "The suspension was filtered"}, {"type": "WASH", "details": "the alumina pad was washed through with 5% methanol in chloroform", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the combined filtrates were evaporated"}, {"type": "CUSTOM", "details": "the residue was triturated with a little chloroform", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "WORKUP"}]}}, {"type": "DISSOLUTION", "details": "The white solid was dissolved in dioxan (50 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dioxan"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WAIT", "details": "left"}, {"type": "CUSTOM", "details": "An impurity precipitated out"}, {"type": "FILTRATION", "details": "this was filtered off"}, {"type": "ADDITION", "details": "Water was added (200 ml) to the filtrate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the solid produced"}, {"type": "FILTRATION", "details": "was filtered off"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}, {"type": "ADDITION", "details": "The fractions containing product"}, {"type": "CUSTOM", "details": "evaporated to dryness"}, {"type": "CUSTOM", "details": "triturated with methanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 24.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2-acetamido-4-(3-nitrophenyl)-4H-naphtho[1,2-b]pyran-3-carbonitrile"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Indomethacin (10 g; 0.028 mol) in 150 mL THF was treated with triethylamine (4.8 mL; 0.035 mol) and cooled to -10° C. Isobutylchloroformate (4.4 mL; 0.033 mol) was added and the reaction was stirred at -10° C. for 10 min. The ice bath was removed and NH3 was bubbled through the solution for 15 min. The resulting pale yellow solid was collected, slurried in CH2Cl2 and filtered again. The product was used with no further purification. ### ORD JSON:

{"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Indomethacin"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 4.8, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Isobutylchloroformate"}], "amount": {"volume": {"value": 4.4, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": -10.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the reaction was stirred at -10\u00b0 C. for 10 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The ice bath was removed", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ice"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "NH3 was bubbled through the solution for 15 min", "duration": {"value": 15.0, "units": "MINUTE"}, "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NH3"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The resulting pale yellow solid was collected"}, {"type": "FILTRATION", "details": "filtered again"}, {"type": "CUSTOM", "details": "The product was used with no further purification"}], "outcomes": [{"reaction_time": {"value": 10.0, "units": "MINUTE"}, "products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Synthesized from 1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester and Naphthalen-2-ol in analogy to Example D-20 d); MS-(+)-ion: M+1=388.1. ### ORD JSON:

{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-chloro-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Naphthalen-2-ol"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of zinc dust (300 mg) in dimethylacetamide (DMA) (0.3 mL) at 50° C. was treated with a solution of chlorotrimethylsilane/1,2-dibromoethane (7/5 v/v, 0.04 mL) and the reaction was stirred at room temperature for 30 minutes. A solution of methyl 2-(tert-butoxycarbonylamino)-3-iodopropanoate (247 mg, 0.75 mmol) in DMA (1 mL) was slowly added and the reaction was stirred for 40 minutes. This mixture was added to a mixture of 95G (35 mg), PdCl2(dppf)2 (7 mg), and CuI (10 mg) in DMA (0.8 mL). The reaction was heated to 80° C. for 18 hours. Water was added and the solid precipitate was collected by filtration. The solid was treated with 33% HBr/AcOH and then concentrate. The residue was dissolved in THF/MeOH and water and treated with LiOH and stirred at room temperature for two hours. The reaction mixture was neutralized with trifluoroacetic acid and purified by preparative reversed phase HPLC to afford the desired product (1.7 mg). Compound 103 had an analytical HPLC retention time=2.906 min. (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 ml/min, monitoring at 220 nm) and a LC/MS M++1=528+. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "reaction_role": "REACTANT"}]}, "m8_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "dimethylacetamide"}], "amount": {"volume": {"value": 0.3, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "zinc"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "chlorotrimethylsilane 1,2-dibromoethane"}], "amount": {"volume": {"value": 0.04, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3_m9_m10_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "95G"}], "amount": {"mass": {"value": 35.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMA"}], "amount": {"volume": {"value": 0.8, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "PdCl2(dppf)2"}], "amount": {"mass": {"value": 7.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}, {"identifiers": [{"type": "NAME", "value": "CuI"}], "amount": {"mass": {"value": 10.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}, "m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 2-(tert-butoxycarbonylamino)-3-iodopropanoate"}], "amount": {"mass": {"value": 247.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMA"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the reaction was stirred at room temperature for 30 minutes"}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "the reaction was stirred for 40 minutes", "duration": {"value": 40.0, "units": "MINUTE"}}, {"type": "TEMPERATURE", "details": "The reaction was heated to 80\u00b0 C. for 18 hours", "duration": {"value": 18.0, "units": "HOUR"}, "temperature": {"setpoint": {"value": 80.0, "units": "CELSIUS"}}}, {"type": "FILTRATION", "details": "the solid precipitate was collected by filtration"}, {"type": "ADDITION", "details": "The solid was treated with 33% HBr/AcOH", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "HBr AcOH"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrate"}, {"type": "DISSOLUTION", "details": "The residue was dissolved in THF/MeOH", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "THF MeOH"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "water and treated with LiOH", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "LiOH"}], "reaction_role": "WORKUP"}]}}, {"type": "STIRRING", "details": "stirred at room temperature for two hours", "duration": {"value": 2.0, "units": "HOUR"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "purified by preparative reversed phase HPLC"}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.7, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 4.8}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 5,7,6,8-tetrahydro-4-[(2-methylpropyl)amino]-3-nitroquinolin-2-yl trifluoromethanesulfonate (4.0 g, 0.01 mole), dibenzylamine (1.9 mL, 0.01 mole), triethylamine (1.4 mL, 0.01 mole) and benzene (100 mL) were combined and heated at reflux for 36 hours. The benzene was evaporated under vacuum and the residue purified by silica gel chromatography eluting with hexane:ethyl acetate 70:30 to provide 4.1 g of the desired product as a viscous orange oil. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "benzene"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5,7,6,8-tetrahydro-4-[(2-methylpropyl)amino]-3-nitroquinolin-2-yl trifluoromethanesulfonate"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "dibenzylamine"}], "amount": {"volume": {"value": 1.9, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 1.4, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "heated"}, {"type": "TEMPERATURE", "details": "at reflux for 36 hours", "duration": {"value": 36.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "The benzene was evaporated under vacuum", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "benzene"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the residue purified by silica gel chromatography"}, {"type": "WASH", "details": "eluting with hexane:ethyl acetate 70:30", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane ethyl acetate"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 4.1, "units": "GRAM"}}}], "isolated_color": "viscous orange", "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 20 μL of acetyl chloride was added to a solution of 90 mg of 2-amino-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide in 2 mL of pyridine at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with MeOH and evaporated. The product was purified on reverse phase HPLC to yield 2-acetamido-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide. MS (Q1) 444.0 (M)+. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "acetyl chloride"}], "amount": {"volume": {"value": 20.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-amino-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide"}], "amount": {"mass": {"value": 90.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "stirred for 2 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The reaction was quenched with MeOH", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MeOH"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated"}, {"type": "CUSTOM", "details": "The product was purified on reverse phase HPLC"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2-acetamido-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a stirred solution of (E)-2-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)phenoxy)isoindoline-1,3-dione (CI.2 g, 0.4 mmol) in EtOH was added hydrazine hydrate (0.1 g, 1.9 mmol), and the resultant reaction mixture was heated at 90° C. for 1 h. The reaction mixture was filtered, and the filtrate was concentrated. The residue was dissolved in CH2Cl2. washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the crude title compound as a gummy liquid (0.08 g, 53%): 1H NMR (400 MHz, CDCl3) δ 7.40 (s, 2H), 6.98 (s, 1H), 6.82 (s, 2H), 6.48 (m, 1H), 6.20 (m, 1H), 5.02 (s, 1H), 4.08 (m, 1H); ESIMS m/z 394.94 ([M−H]−). ### ORD JSON:

{"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(E)-2-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)phenoxy)isoindoline-1,3-dione"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrazine hydrate"}], "amount": {"mass": {"value": 0.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "EtOH"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 90.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the resultant reaction mixture"}, {"type": "FILTRATION", "details": "The reaction mixture was filtered"}, {"type": "CONCENTRATION", "details": "the filtrate was concentrated"}, {"type": "DISSOLUTION", "details": "The residue was dissolved in CH2Cl2", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "crude title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.08, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 53.0}}], "isolated_color": "gummy", "texture": {"type": "CUSTOM", "details": "liquid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: The title compound is prepared analogously to Example 1c) from 3-(4-trifluoroacetyl-3-hydroxy-2-propylphenoxy)-propyl bromide and triphenylphosphine; m.p. 170°-190° C. ### ORD JSON:

{"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(4-trifluoroacetyl-3-hydroxy-2-propylphenoxy)-propyl bromide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triphenylphosphine"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a stirred -78° C. solution in THF (200 mL) under argon of 2-[5-(4-fluorophenoxy)-2-furyl]-1,1-dibromoethene (23.1 g, 63.81 mmol), prepared as in step 2, was added n-butyl lithium (51.0 mL, 127.62 mmol, 2.5M in hexanes). The reaction was stirred for 0.5 hours at -78° C. Aqueous ammonium chloride was added to the cold reaction, the ice bath was removed and the reaction mixture allowed to warm to room temperature. The majority of THF was removed in vacuo. The resulting mixture was partitioned between water and ether. The combined ether layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (hexanes) to give 6.5 g (50%) of 2-[5-(4-fluorophenoxy)-2-furyl]-ethyne. ### ORD JSON:

{"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "n-butyl lithium"}], "amount": {"volume": {"value": 51.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m4_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[5-(4-fluorophenoxy)-2-furyl]-1,1-dibromoethene"}], "amount": {"mass": {"value": 23.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": -78.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction was stirred for 0.5 hours at -78\u00b0 C"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the ice bath was removed", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ice"}], "reaction_role": "WORKUP"}]}}, {"type": "TEMPERATURE", "details": "to warm to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "The majority of THF was removed in vacuo", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "THF"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The resulting mixture was partitioned between water and ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The combined ether layers were dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "The residue was purified by chromatography on silica gel (hexanes)"}], "outcomes": [{"reaction_time": {"value": 0.5, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2-[5-(4-fluorophenoxy)-2-furyl]-ethyne"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 6.5, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 50.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 50.4}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of N-(4-cyanophenyl)-2,2,2-trifluoro-N-(5,6,7,8-tetrahydro-6-oxo-1-naphthyl)acetamide (1.17 g, 3.27 mmol) in THF (15 ml) was added dropwise over a 15 minute period to a stirred suspension of 80% NaH (0.30 g, 10 mmol) (Aldrich) in methyl cyanoformate (1.5 ml, 19 mmol) (Aldrich) and THF (15 ml) under nitrogen. The reaction mixture was stirred 30 minutes at room temperature then quenched with acetic acid (0.7 ml, 12 mmol). The solution was concentrated in vacuo onto silica gel (3 g) and the absorbed material purified by chromatography on silica gel (30 g) eluting with ether:hexane (1:4 to 1:3) to give methyl 5-(N-(4-cyanophenyl)-2,2,2-trifluoroacetamido)-3,4-dihydro-2-hydroxy-naphthalene carboxylate (0.64 g). 1H NMR (CDCl3, 200 MHz) δ: 2.5-2.9 (m, 4H, CH2CH2), 3.93 (s, 3H, CH3), 7.10 (d, J=8 Hz, 1H, Ar), 7.32 (t, J=8 Hz, 1H, Ar), 7.39 (d, J=9 Hz, 2H, Ar), 7.64 (d, J=9 Hz, 2H, Ar), 7.82 (d, J=8 Hz, 1H, Ar), 13.35 (s, 1H, OH). Anal. Calculated for C21H15F3N2O4: C, 60.58; H, 3.63; N, 6.73. Found: C, 60.66; H, 3.66; N, 6.68. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 0.7, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(4-cyanophenyl)-2,2,2-trifluoro-N-(5,6,7,8-tetrahydro-6-oxo-1-naphthyl)acetamide"}], "amount": {"mass": {"value": 1.17, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaH"}], "amount": {"mass": {"value": 0.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl cyanoformate"}], "amount": {"volume": {"value": 1.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred 30 minutes at room temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The solution was concentrated in vacuo onto silica gel (3 g)"}, {"type": "CUSTOM", "details": "the absorbed material purified by chromatography on silica gel (30 g)"}, {"type": "WASH", "details": "eluting with ether:hexane (1:4 to 1:3)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "methyl 5-(N-(4-cyanophenyl)-2,2,2-trifluoroacetamido)-3,4-dihydro-2-hydroxy-naphthalene carboxylate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.64, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: (±)-2,6-Di-tert-butyl-4-methoxyphenyl-4-[N-{(3RS,4RS)-N,3-dimethyl-4-piperidinyl}phenylamino]benzoate (6b) (7.38 g, 13.62 mmol) was transesterified with sodium methoxide (t35 mmol) in toluene (150 mL) and NMP (40 mL) and then hydrolyzed with MeOH and H2O (12:1, 165 mL) as before. The resulting acid was dissolved in THF (200 mL) with triethylamine (5 mL), diethylamine (2 mL), and BOP reagent (6.1 g, 13.80 mmol) as above. Work-up and chromatography on silica gel as above afforded 7b (3.02 g, 59%) as a yellow liquid. Conversion to the hydrochloride salt was done with 1 N HCl in ether. 1H NMR (CD3OD) δ 1.10-1.25 (m, 12H), 1.76-2.28 (s, 3H), 2.99 (t, 1H, J=12.5 Hz), 3.12-3.29 (m, 1H), 3.31-3.58 (m, 7H), 4.12-4.29 (m, 1H), 6.78 (d, 2H, J=8.8 Hz), 7.18 (d, 2H, J=7.3 Hz), 7.22 (d, 2H, J=8.8 Hz), 7.33 (t, 1H, J=7.4 Hz), 7.48 (t, 2H, J=7.5 Hz); 13C NMR (CD3OD) δ 16.1, 29.0, 35.3, 43.8, 55.3, 58.7, 60.7, 116.9, 127.3, 127.8, 129,1, 130.7, 131.2, 144.0, 152.0, 173.9. Anal. (C24H34ClN3O.1.25H2O): C, H, N. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(\u00b1)-2,6-Di-tert-butyl-4-methoxyphenyl-4-[N-{(3RS,4RS)-N,3-dimethyl-4-piperidinyl}phenylamino]benzoate"}], "amount": {"mass": {"value": 7.38, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m7_m8_m9_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "BOP reagent"}], "amount": {"mass": {"value": 6.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "diethylamine"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m10": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 165.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "MeOH"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "NMP"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium methoxide"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "7b"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 3.02, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 59.0}}], "isolated_color": "yellow", "texture": {"type": "CUSTOM", "details": "liquid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To 2-[3-(2-bromomethyl-4-trifluoromethyl-phenoxy)-phenyl]-propionic acid (0.042 g, 0.10 mmol) and 2-oxazolidone (0.018 g, 0.21 mmol) in DMF was added sodium hydride (60% in mineral oil; 0.008 g, 0.21 mmol), and the reaction was stirred at room temperature for 30 minutes. The mixture was partitioned between H2O and EtOAc, and the aqueous layer was acidified and purified by preparative HPLC to give the desired product. ### ORD JSON:

{"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[3-(2-bromomethyl-4-trifluoromethyl-phenoxy)-phenyl]-propionic acid"}], "amount": {"mass": {"value": 0.042, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-oxazolidone"}], "amount": {"mass": {"value": 0.018, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "amount": {"mass": {"value": 0.008, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the reaction was stirred at room temperature for 30 minutes"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The mixture was partitioned between H2O and EtOAc", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "purified by preparative HPLC"}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of aluminium tribromide (3.85 g) in nitromethane was added in portions to a stirred solution of benzyl 2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (1.93 g) and anisole (3.1 g) in dichloromethane at 0° C. under an inert atmosphere. The reaction mixture was stirred at 0° C. for 10 minutes and at ambient temperature for 2 hours and diluted with dichloromethane. The dichloromethane solution was washed in turn with 2 M hydrochloric acid and with water. The organic solution was extracted with 1 M sodium bicarbonate, the aqueous extract was then washed with diethyl ether and acidified to pH 1 with 2 M hydrochloric acid. The acidic solution was extracted with ethyl acetate, the extract was dried (magnesium sulphate) and evaporated under reduced pressure to give 2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1, 3-oxazin-3-yl)-2-methylpropanoic acid (0.70 g) as a pink solid, m.p. 149-151° C. ### ORD JSON:

{"inputs": {"m1_m4_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "aluminium tribromide"}], "amount": {"mass": {"value": 3.85, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzyl 2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate"}], "amount": {"mass": {"value": 1.93, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "anisole"}], "amount": {"mass": {"value": 3.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "nitromethane"}], "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "SOLVENT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}, "setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at 0\u00b0 C. for 10 minutes and at ambient temperature for 2 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "The dichloromethane solution was washed in turn with 2 M hydrochloric acid and with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "The organic solution was extracted with 1 M sodium bicarbonate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "the aqueous extract"}, {"type": "WASH", "details": "was then washed with diethyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "The acidic solution was extracted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "the extract was dried (magnesium sulphate)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulphate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated under reduced pressure"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1, 3-oxazin-3-yl)-2-methylpropanoic acid"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.7, "units": "GRAM"}}}], "isolated_color": "pink", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 15.0 g of 4-chloro-6,7-bis(2-methoxyethoxy) quinazoline was suspended in 450 ml ethanol and 13.8 g of 3-aminophenyl acetylene was added at 25-30° C. Further 3.0 g tartaric acid was added. The reaction mass was stirred at 25-30° C. for 6 hours. Solid obtained was filtered, washed with water and dried under vacuum. This solid was suspended in water, basified with potassium hydroxide and stirred for 10 minutes. The resulting erlotinib base was isolated by filtration, washed with ethanol and dried under vacuum. The solid obtained was then suspended in water and acidified to pH 1.0-2.0 using hydrochloric acid. The reaction mixture was stirred for 2 hours, filtered, washed with water and dried at 40-45° C. to obtain 18.3 g of erlotinib hydrochloride. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 450.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-6,7-bis(2-methoxyethoxy) quinazoline"}], "amount": {"mass": {"value": 15.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-aminophenyl acetylene"}], "amount": {"mass": {"value": 13.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "tartaric acid"}], "amount": {"mass": {"value": 3.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 27.5, "precision": 2.5, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mass was stirred at 25-30\u00b0 C. for 6 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Solid obtained"}, {"type": "FILTRATION", "details": "was filtered"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried under vacuum"}, {"type": "STIRRING", "details": "stirred for 10 minutes", "duration": {"value": 10.0, "units": "MINUTE"}}], "outcomes": [{"reaction_time": {"value": 6.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "erlotinib base"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2-(Perfluorooctyl)ethanethiol (RF =C8F17, 4.80 g, 10.0 mmle) and 1,2-dichloroethane (29.67 g, 300 mmole) and 10 ml of water was stirred by magnet bar under nitrogen at ambient temperature, while sodium hydroxide (0.67 g, 16.7 mmole) in 20 ml of water was added dropwise during a half hour. An exotherm carried the temperature from 24.0° to 25.2°. A thick, white slurry was formed. After 5 hours of stirring at 23.5°, the white slurry had not separated into two liquid layers as in the procedures used above. Stirring was continued for 29 hours and a sample removed for analysis. After 39 hours the thick white paste was made acidic by the addition of 5.0 ml of 6N hydrochloric acid, and the white solid collected on a Buchner funnel, and washed with water. When dry the solid weighed 3.45 g, mp (sinter 82°) 83°-88°, 70% of theory for C8F17CH2CH2SCH2CH2SCH2CH2C8F17. A 1.00-g sample was recrystallized from hot chloroform, that was first filtered while hot, from insoluble salt; 0.54 g, mp (sinter 90°) 92°-94°. The filtrate deposited 0.26 g of less pure solid. The original filtrate containing water and 1,2-dichloroethane (above) was separated into layers, and the organic layer evapd off to give white solid, mp 30°-33°, 1.18 g, 21.7% of theory for C8F17CH2CH2SCH2CH2Cl. ### ORD JSON:

{"inputs": {"m1_m2_m5_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(Perfluorooctyl)ethanethiol"}], "amount": {"mass": {"value": 4.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1,2-dichloroethane"}], "amount": {"mass": {"value": 29.67, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"mass": {"value": 0.67, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "After 5 hours of stirring at 23.5\u00b0"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "was added dropwise during a half hour"}, {"type": "CUSTOM", "details": "from 24.0\u00b0 to 25.2\u00b0"}, {"type": "CUSTOM", "details": "A thick, white slurry was formed"}, {"type": "CUSTOM", "details": "the white slurry had not separated into two liquid layers as in the procedures"}, {"type": "STIRRING", "details": "Stirring"}, {"type": "WAIT", "details": "was continued for 29 hours", "duration": {"value": 29.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "a sample removed for analysis"}, {"type": "ADDITION", "details": "After 39 hours the thick white paste was made acidic by the addition of 5.0 ml of 6N hydrochloric acid", "duration": {"value": 39.0, "units": "HOUR"}, "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the white solid collected on a Buchner funnel"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "When dry the solid"}, {"type": "CUSTOM", "details": "3.45 g, mp (sinter 82\u00b0) 83\u00b0-88\u00b0, 70% of theory"}, {"type": "CUSTOM", "details": "A 1.00-g sample was recrystallized from hot chloroform, that", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "was first filtered while hot, from insoluble salt"}, {"type": "CUSTOM", "details": "0.54 g, mp (sinter 90\u00b0) 92\u00b0-94\u00b0"}, {"type": "ADDITION", "details": "The original filtrate containing water and 1,2-dichloroethane (above)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "1,2-dichloroethane"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "was separated into layers"}], "outcomes": [{"reaction_time": {"value": 5.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "C8F17CH2CH2SCH2CH2Cl"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of methyl {(1R)-2-[(2S)-2-(9-{2-[(2S,4S)-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate (55 mg, 0.077 mmol), (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (14 mg, 0.077 mmol), HATU (32 mg, 0.085 mmol) and 0.4 mL 10% DIPEA in DMF was stirred at room temperature for 1 hour. The product was purified by reverse phase HPLC. The product was converted to the free base by dissolution in 2 mL 1:1 acetonitrile:methanol and passage through a prepacked cartridge of polymer supported carbonate. The eluent was concentrated, the taken up in 10% TFA in 1:1 acetonitrile:water, frozen, and lyophilized to give the product as a trifluoroacetate salt. (30.7 mg) ### ORD JSON:

{"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl {(1R)-2-[(2S)-2-(9-{2-[(2S,4S)-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}-1,11-dihydroisochromeno[4\u2032,3\u2032:6,7]naphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate"}], "amount": {"mass": {"value": 55.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(S)-2-(methoxycarbonylamino)-3-methylbutanoic acid"}], "amount": {"mass": {"value": 14.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HATU"}], "amount": {"mass": {"value": 32.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DIPEA"}], "amount": {"volume": {"value": 0.4, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "was stirred at room temperature for 1 hour"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The product was purified by reverse phase HPLC"}, {"type": "DISSOLUTION", "details": "The product was converted to the free base by dissolution in 2 mL 1:1 acetonitrile", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "The eluent was concentrated"}, {"type": "TEMPERATURE", "details": "water, frozen", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "trifluoroacetate"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a sealed tube were added N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(6-chloro-5-methylpyridin-3-yl)acetamide 148-1 (123 mg, 0.32 mmol), 2-(trifluoromethyl)pyridin-4-ylboronic acid (61 mg, 0.32 mmol), Pd(OAc)2 (3.6 mg, 0.016 mmol), 2,6-Dimethoxy-1,1′-biphenyl-2-yl)dicyclohexylphosphine (13.0 mg, 0.032 mmol) and K3PO4 (202 mg, 0.95 mmol). The tube and its contents were then purged with nitrogen. After degassed toluene (1.0 mL) was added, the mixture was stirred at 120° C. overnight. After cooling to room temperature, the mixture was poured into water and extracted with ethyl acetate (8 mL×3). The combined organic phases were dried over Na2SO4, and concentrated. The residue was purified by reverse phase HPLC to give to give N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(3-methyl-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)acetamide 222. MS m/z 498.8 (M+1); 1H NMR 400 MHz (CDCl3) δ 8.81 (d, 1H), 8.51 (d, 1H), 8.35 (s, 1H), 8.11 (d, 1H), 7.91 (s, 1H), 7.89 (s, 1H), 7.68-7.64 (m, 2H), 7.30 (dd, 1H), 3.80-3.75 (m, 4H), 3.63 (t, 2H), 3.14 (t, 2H), 3.11 (t, 2H), 2.39 (s, 3H), 2.14 (s, 3H). ### ORD JSON:

{"inputs": {"m1_m2_m5_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(6-chloro-5-methylpyridin-3-yl)acetamide"}], "amount": {"mass": {"value": 123.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-(trifluoromethyl)pyridin-4-ylboronic acid"}], "amount": {"mass": {"value": 61.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dicyclohexylphosphine"}], "amount": {"mass": {"value": 13.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "K3PO4"}], "amount": {"mass": {"value": 202.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd(OAc)2"}], "amount": {"mass": {"value": 3.6, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 120.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at 120\u00b0 C. overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The tube and its contents were then purged with nitrogen"}, {"type": "CUSTOM", "details": "After degassed toluene (1.0 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "was added"}, {"type": "TEMPERATURE", "details": "After cooling to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "ADDITION", "details": "the mixture was poured into water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with ethyl acetate (8 mL\u00d73)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 8.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The combined organic phases were dried over Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated"}, {"type": "CUSTOM", "details": "The residue was purified by reverse phase HPLC"}, {"type": "CUSTOM", "details": "to give"}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(3-methyl-2\u2032-(trifluoromethyl)-2,4\u2032-bipyridin-5-yl)acetamide"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: The title compound (134 mg) was prepared according to Example 281 using 200 mg of 2-cyclopropyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 281, Step C) and 84 mg of 3-thiopheneboronic acid. MS (ESI): exact mass calculated for C14H17N3S, 259.11. found, m/z 260.4 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.64-7.63 (m, 2H), 7.31-7.29 (m, 1H), 4.65 (br s, 1H), 3.70-3.60 (br s, 1H), 3.57-3.52 (m, 1H), 3.40-3.38 (m, 1H), 3.19 (br s, 1H), 3.13-3.11 (m, 1H), 2.99-2.96 (m, 1H), 2.91-2.89 (m, 1H), 0.93-0.88 (m, 4H). ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-cyclopropyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-thiopheneboronic acid"}], "amount": {"mass": {"value": 84.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 134.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: N,2-Dimethoxy-N-methyl-2-(1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)acetamide was coupled with 2-(4-bromo-3,5-dimethoxyphenyl)furan according to the procedure for the synthesis of Example 13. Purification by chromatography provided 1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)ethanone as a light yellow foam (0.153 g, 34% yield). MS: m/z 486.1 [M+1-1]+. ### ORD JSON:

{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N,2-Dimethoxy-N-methyl-2-(1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)acetamide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-(4-bromo-3,5-dimethoxyphenyl)furan"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Purification by chromatography"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "1-(5-(4-bromo-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(1-methyl-1H-benzo[d][1,2,3]triazol-5-yl)ethanone"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.153, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 34.0}}], "isolated_color": "light yellow", "texture": {"type": "FOAM", "details": "foam"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Concentrated hydrochloric acid (21.5 ml) was added to a solution of the product of step (a) (9.3 g) in ethanol (65 ml). The mixture was heated at 50° C. for 1 h, cooled and the solvent was evaporated. Toluene (3×50 ml) was added to the residue and was evaporated after each addition. The residue was triturated with diisopropyl ether (80 ml) to give the title compound (Intermediate 12) as a pale brown powder (6.8 g) m.p. 158°-159° C. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 21.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 9.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 65.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 50.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "cooled"}, {"type": "CUSTOM", "details": "the solvent was evaporated"}, {"type": "ADDITION", "details": "Toluene (3\u00d750 ml) was added to the residue", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Toluene"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "was evaporated"}, {"type": "ADDITION", "details": "after each addition"}, {"type": "CUSTOM", "details": "The residue was triturated with diisopropyl ether (80 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diisopropyl ether"}], "amount": {"volume": {"value": 80.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 6.8, "units": "GRAM"}}}], "isolated_color": "pale brown", "texture": {"type": "POWDER", "details": "powder"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: In an ice bath, ethyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-aminonaphthalene-2-carboxylate (Compound C, 150 mg, 0.55 nmol) was added 0.24 ml of HBF4 (48% solution in water), followed by a solution of NaNO2 (81 mg, 1.16 mmol) in 1 ml of water. The slurry was left in a refrigerator for 3 days. The reaction mixture was washed successively with ethyl acetate until TLC showed no UV visible spot at the baseline. The ethyl acetate layer was dried with MgSO4 and the solution was concentrated to an oil. The oil was further dissolved in 1 ml of toluene and the mixture was heated under reflux for 2 h. After the reaction cooled to room temperature, solvent was evaporated and the residue was passed through a column (silica gel, ethyl acetate/hexane 1/10) to give the title compound as an oil. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NaNO2"}], "amount": {"mass": {"value": 81.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-aminonaphthalene-2-carboxylate"}], "amount": {"mass": {"value": 150.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Compound C"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HBF4"}], "amount": {"volume": {"value": 0.24, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "The reaction mixture was washed successively with ethyl acetate until TLC", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The ethyl acetate layer was dried with MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "the solution was concentrated to an oil"}, {"type": "DISSOLUTION", "details": "The oil was further dissolved in 1 ml of toluene", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "TEMPERATURE", "details": "the mixture was heated"}, {"type": "TEMPERATURE", "details": "under reflux for 2 h", "duration": {"value": 2.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "solvent was evaporated"}], "outcomes": [{"reaction_time": {"value": 3.0, "units": "DAY"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: N-(4-Methanesulfonylamino-2-sulfamoyl-phenyl)-malonamic acid ethyl ester (Example 17e, 9.55 g, 26.16 mmol) was dissolved in 8% aqueous sodium hydroxide solution (262 mL) and heated at 100° C. for 1.5 h. The reaction mixture was cooled to 0° C. and the solution was acidified by slowly adding 12.0 M aqueous hydrochloric acid solution until pH 1-2 was reached. A precipitate started to form and the suspension was allowed to stir for 30 min at 0° C. The precipitate was collected by vacuum filtration, washed with cold water, and dried under high vacuum to afford (7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (7.20 g, 21.621 mmol, 82.6% yield) as a pinkish solid. 1H NMR (400 MHz, DMSO-d6) δ: 3.03 (3H, s), 3.56 (2H, s), 7.33 (1H, d, J=9.1 Hz), 7.52-7.54 (2H, m), 10.09 (1H, s), 12.24 (1H, s), 13.02 (1H, bs). LC-MS (ESI) calcd for C10H11N3O6S2 333.01, found 334.1 [M+H+]. ### ORD JSON:

{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(4-Methanesulfonylamino-2-sulfamoyl-phenyl)-malonamic acid ethyl ester"}], "amount": {"mass": {"value": 9.55, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 262.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "to stir for 30 min at 0\u00b0 C"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The reaction mixture was cooled to 0\u00b0 C.", "temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}}, {"type": "CUSTOM", "details": "to form"}, {"type": "FILTRATION", "details": "The precipitate was collected by vacuum filtration"}, {"type": "WASH", "details": "washed with cold water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried under high vacuum"}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1\u03bb6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid"}], "measurements": [{"type": "AMOUNT", "details": "AMOUNT", "amount": {"moles": {"value": 21.621, "units": "MILLIMOLE"}}}, {"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 7.2, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 82.6}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 82.6}}], "isolated_color": "pinkish", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: The 2,5-dihydroxy benzoquinone copper (II) polymer, (Table I, compound 5), Cu(DHBQ) is prepared as follows: Ten g of 2,5-dihydroxy benzoquinone are dissolved in 200 ml of either dimethylformamide (DMF) or tetrahydrofurane (THF). To this is added 14 g of copper acetate (hydrate) dissolved in 250 ml of DMF (or THF). The solution is refluxed for 4 hours. The products have to be centrifuged after being allowed to settle for a few days. The DMF solution yielded a brown product, and the THF yielded a blue product. Since the compounds were insoluble in all common solvents, purification and analysis was difficult. The only purification attempted was Soxhlet extraction using acetone as suggested by Coble and Holizclaw, J. Inorg, Nucl. Chem., 36,1049 (1974). The yield was about 10 g. The chain length is difficult to estimate, but low voltage mass spectral data (20 eV, CEC 450) show masses up to at least 600, indicating the molecule to be at least a trimer. The analytical data indicate copper=31.52% (found 30.2%); carbon=35.58% (found 37.88%; hydrogen=0.99% (found 2.39%. The IR spectra shows a carbonyl shift to 1470 cm-1 (from 1640 cm-1 in the starting DHBQ) and a loss of the phenolic absorption of 3300 cm-1. The fragmentation pattern from a high voltage (70 eV) mass spectral study is shown in Table III. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "copper acetate"}], "amount": {"mass": {"value": 14.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "THF"}], "reaction_role": "REACTANT"}]}, "m2_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "2,5-dihydroxy benzoquinone"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylformamide"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m9": {"components": [{"identifiers": [{"type": "NAME", "value": "DMF"}], "reaction_role": "SOLVENT"}]}, "m8_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "THF"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrahydrofurane"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The solution is refluxed for 4 hours", "duration": {"value": 4.0, "units": "HOUR"}}, {"type": "WAIT", "details": "to settle for a few days"}, {"type": "CUSTOM", "details": "Since the compounds were insoluble in all common solvents, purification and analysis"}, {"type": "CUSTOM", "details": "The only purification"}, {"type": "EXTRACTION", "details": "Soxhlet extraction"}, {"type": "CUSTOM", "details": "a loss of the phenolic absorption of 3300 cm-1"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "compound 5"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "Cu(DHBQ)"}], "reaction_role": "PRODUCT"}]}]}