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Here is a chemical reaction formula: Reactants are m1_m5_m2_m7:FC(C(=O)OC(C(F)(F)F)=O)(F)F, amount is: 0.0 ;m1_m5_m2_m7:CS(=O)C, amount is: 0.0 ;m4:C(C)N(CC)CC, amount is: 0.0 ;m3_m6:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC(O)C1=CCCC1)OC)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m7:C(Cl)Cl, amount is: 0.0 ;m1_m5_m2_m7:C(Cl)Cl, amount is: 0.0 ;m3_m6:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CCCC1)C(=O)CC=1C(=C2C(OCC2=C(C1OC)C)=O)O[Si](C)(C)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Trifluoroacetic anhydride (1.6 ml) in methylene chloride (3.6 ml) was added dropwise to dimethyl sulfoxide (1.05 ml) and CH2Cl2 (7.5 ml) under nitrogen over 5 minutes at -60° C. and stirred for 30 minutes. After addition of (±)-2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-1-cyclopentenyl-1-hydroxyethane (2 g) in methylene chloride (6 ml) over 15 minutes, the mixture was warmed to -40° C. over 1 hour. Triethylamine (10 ml) was added at -70° C., the cooling bath was removed, and after reaching ambient temperature the solution was diluted with ethyl acetate, washed twice with saturated aqueous potassium dihydrogen phosphate, brine, dried and evaporated. The solid residue was chromatographed on silica gel with 7:1 hexane, eluting with ethyl acetate to afford cyclopentenyl (4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-ylmethyl) methanone (1.65 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC(O)C1=CCCC1)OC)C)=O, amount is: 0.0 ;m1_m3_m2:C(C(C)(C)C)(=O)O, amount is: 0.0 ;m1_m3_m2:C(C)C(C([O-])([O-])[O-])(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C\C=C/1\C(CCC1)CC(=O)OCC)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1-[2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-1-hydroxyeth-1-yl]cyclopent-1-ene (0.22 g) in triethylorthoacetate (10 ml) was treated with pivalic acid (0.010 g) and then heated to 100° C., and maintained at that temperature for 18 hours. After cooling to ambient temperature, the solution was diluted with 1:1 ethyl acetate:hexanes and washed sequentially with water, saturated aqueous sodium bicarbonate, and brine. Drying over magnesium sulfate was followed by evaporation; chromatography of the residue on silica gel (10% ethyl acetate in hexanes) afforded ethyl (E) 2-[2-[2-[4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl]ethylidene]-cyclopent-1-yl]acetate (0.11 g) as an oil. |
Here is a chemical reaction formula: Reactants are m4_m8:[Cl-].[NH4+], amount is: 0.0 ;m3:CI, amount is: 0.0 ;m1_m5_m6_m2_m7:C[Si](C)(C)[N-][Si](C)(C)C.[Na+], amount is: 0.0 MOLE;m1_m5_m6_m2_m7:OC1=C2C(OCC2=C(C(=C1C\C=C/1\[C@@H](CCC1)CC(=O)OCC)OC)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m8:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m5_m6_m2_m7:O1CCCC1, amount is: 0.0 ;m1_m5_m6_m2_m7:CN1C(N(CCC1)C)=O, amount is: 0.0 ;m1_m5_m6_m2_m7:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1=C2C(OCC2=C(C(=C1C\C=C/1\[C@@H](CCC1)C(C(=O)OCC)C)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1M sodium bis (trimethylsilyl)amide in tetrahydrofuran (31.7 ml) and 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H)-pyrimidinone (2.74 ml) at -78° C. was added ethyl (E) 2-{2-[2-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)ethylidene]cyclopent-1-(S)-yl}acetate (3.39 g) in tetrahydrofuran (35 ml), over a period of 30 minutes. After an additional 30 minutes methyl iodide (2.25 ml) was added. After an additional two hours saturated aqueous ammonium chloride (10 ml) and ethyl acetate were added. The organic solution was dried and evaporated and the residue chromatographed on silica gel, eluting with 4:1 hexane:ethyl acetate, to afford one diastereomer of ethyl (E) 2-{2-[2-(1,3-dihydro-4-hydroxy 6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)ethylidene]cyclopent-1-(S)-yl}propionate as a low-melting solid. |
Here is a chemical reaction formula: Reactants are m1:COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC=C(C(C=C)=O)C, amount is: 0.0 MOLE;m2:B(F)(F)F.CCOCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(C)(=O)OCC, amount is: 0.0 MOLE;m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The solid product prepared in Example ZC-1C, 6-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl)-4-methylhexa-1,4-dien-3-one was dissolved in methylene chloride (15 mL) and treated with boron trifluoride etherate (0.5 mL). After 0.5 hours, the reaction was diluted with ethyl acetate and washed with brine, then dried over magnesium sulfate. Filtration, solvent removal and chromatography (silica gel, hexanes/methylene chloride/ether, 4/4/2) gave the product, 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5 -isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-one (0.18 g) as a colorless solid m.p. 65.4-66.8 |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 MOLE;m3:Cl(=O)[O-].[Na+], amount is: 0.0 ;m1_m5:COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)CC=O)C, amount is: 0.0 MOLE;m2:C1(O)=CC(O)=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m5:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)CC(=O)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The 3-(1,3-dihydro-6-methoxy-7methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-ylacetaldehyde was dissolved in dioxane (8 mL) and pH 5 buffer (3 mL) and treated with resorcinol (0.10 g). To this mixture was then added sodium chlorite (0.080 g). After 2 minutes, the reaction was diluted with ethyl acetate and made acidic with 5% hydrochloric acid. After two extractions with ethyl acetate, the combined organic layers were dried over magnesium sulfate. The residue, 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-ylacetic acid obtained after solvent removal was carried on without further purification. |
Here is a chemical reaction formula: Reactants are m2:O.[OH-].[Li+], amount is: 0.0 ;m1:COC1=C(C(=C2C(OCC2=C1C)=O)OS(=O)(=O)C1=CC=C(C=C1)C)CC1=C(C(CC1)CC(=O)O)C, amount is: 0.0 MOLE;m3:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4_m5:CO, amount is: 0.0 ;m4_m5:O, amount is: 0.0 ;m6:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:OC1=C2C(OCC2=C(C(=C1CC1=C(C(CC1)CC(=O)O)C)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-ylacetic acid obtained in Example ZC-1G was dissolved in a mixture of methanol (8 mL) and water (2 mL) and treated with lithium hydroxide monohydrate (0.15 g). After 4 hours, the reaction was diluted with ethyl acetate and made acidic with 5% hydrochloric acid. After two extractions with ethyl acetate, the product was washed out of the combined organic layers with 2M NaOH. Acidification of the basic layers with 5% hydrochloric acid and extraction of the product into ethyl acetate was followed by drying the organic layer with magnesium sulfate. Filtration and solvent removal was followed by two flash chromatographies (hexanes/ethyl acetate, 4/1 with 1% HOAc; then methylene chloride/methanol 25/1) to provide 3-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-ylacetic acid (0.010 g) m.p. 153°-159° C. |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 MOLE;m1_m2_m4_m5:C(C)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C/C1=C(C(=O)OC)C=CC=C1C)OC)C)=O, amount is: 0.0 ;m1_m2_m4_m5:[OH-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 MOLE;m1_m2_m4_m5:CO, amount is: 0.0 ;m1_m2_m4_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C/C1=C(C(=O)O)C=CC=C1C)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of methyl (E)-2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate (0.1 g) and lithium hydroxide (0.06 g) in methanol (1 ml) and water (1 ml) was heated at 70° C. for 48 hours. The solution was cooled and poured into water, then acidified with 2N hydrochloric acid and extracted with ethyl acetate. The extract was dried and evaporated to give (E)-2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoic acid, mp 180°-3° C. (ethyl acetate/cyclohexane). |
Here is a chemical reaction formula: Reactants are m1_m3:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC(C(=CCC(C(C(C)(C)C)(O[SiH3])C)C)C)O)OC)C)=O, amount is: 0.0 ;m2:C(C(C)(C)C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)(OCC)(OCC)OCC, amount is: 0.0 ;m4:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCO[Si](C)(C)C(C)(C)C)\C)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 7-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-1-tert-butyldimethyl-silyloxy-6-hydroxy-5-methylhept-4-ene (4.74 g) was dissolved in triethyl orthoacetate (76 ml) and pivalic acid (171mg) was added. The solution was placed in an oil bath preheated to 130° C., and stirred for 21/2 hrs. ter cooling, the reaction was diluted with ether, washed with 1N NaHSO4 (3X), saturated sodium bicarbonate, brine, and dried. The solvent was evaporated and the resulting oil chromatographed on silica gel (20% ethyl acetate in hexanes) to give ethyl (E) 6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-(3-tert-butyldimethylsilyloxypropyl)-4-methylhex-4-enoate (2.94 g), a compound of Formula 802. |
Here is a chemical reaction formula: Reactants are m1_m2:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCO[Si](C)(C)C(C)(C)C)\C)OC)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)#N, amount is: 0.0 ;m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCO)\C)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Ethyl (E) 6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxo-isobenzofuran-5-yl)-3-(3-tert-butyldimethylsilyloxypropyl)-4-methylhex-4-enoate (2.92 g) was dissolved in acetonitrile (50 ml). To this was added a solution of 40% aqueous HF (5 ml) in acetonitrile (45 ml), and the reaction mixture stirred for 10 minutes. Most of the acetonitrile was then evaporated, and the remaining solution diluted with ether. The ether was washed with water, saturated sodium bicarbonate (3X), brine, and dried. Evaporation of the solvent gave an oil which was chromatographed on silica gel (40% ethyl acetate in hexmnes) to give ethyl (E) 6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxo-isobenzofuran-5-yl)-3-(3-hydroxypropyl)-4-methylhex-4-enoate (2.10 g), a compound of Formula 803, as an oil. |
Here is a chemical reaction formula: Reactants are m1_m3:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCBr)\C)OC)C)=O, amount is: 0.0 ;m2_m4:O.O.O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:CCOCC, amount is: 0.0 MOLE;m1_m3:C1CCOC1, amount is: 0.0 ;m2_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)CCCBr)\C)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of of ethyl (E) 6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-(3-bromopropyl)-4-methylhex-4-enoate (1.62 g) was dissolved in THF (25 ml), cooled to 0° C., and a solution of tetrabutylammonium fluoride trihydrate (919 mg) in THF (5 ml) was added. The reaction was stirred for 15 min, diluted with ether, washed water (2X), brine, and dried. The solvent was evaporated, and the resulting oil chromatographed on silica gel (15%-20% ethyl acetate in hexanes) to give ethyl (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy7-methyl-3-oxoisobenzofuran-5-yl)-3-(3-bromopropyl)-4-methylhex-4-enoate (810 mg). |
Here is a chemical reaction formula: Reactants are m1_m4_m2:FC=1C(=C(C(=C(C1)F)F)F)F, amount is: 0.0 ;m1_m4_m2:C(C)(C)(C)[Li].CCCCC, amount is: 0.0 ;m3:FC1=C(C(=C(C(=C1B(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C(C(=C(C(=C1[B-](C1=C(C(=C(C(=C1F)F)F)F)F)(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.[Li+], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of pentafluorobenzene (4.40 g, 26.2 mmol) and diethyl ether (50 ml) was added dropwise a 20 wt. % tertbutyllithium/pentane solution (7.98 g, 25.0 mmol) while Keeping the temperature of the reaction mixture at -55° to -65° C., and, after the completion of dropwise addition, the mixture was stirred for about 0-5 hours while keeping the temperature at -25° to -50 ° C. Thereafter, a 20.0 wt. % tris(pentafluorophenyl)borane/toluene solution (63.8 g, 25.0 mmol) was mixed while keeping the temperature of the reaction mixture at -25° to -40° C., which was stirred for 30 minutes at the same temperature and then the temperature was raised to room temperature. From the solution of lithium tetrakis(pentafluorophenyl)borate thus obtained, diethyl ether was removed by distillation and the organic layer was washed thrice with 20 mL of water. After combining the aqueous layers, 1.1 equivalent to the boron source of aqueous solution of N,N-dimethylanilinium chloride was reacted with the aqueous layer to deposit white crystals. The crystals obtained were filtered, washed with water and then dried under vacuum to obtain N,N-dimethylanilinium tetrakis(pentafluorophenyl)borate in 97.3% yield. When determining the purity by means of 1H and 19F NMR using pentafluorotoluene as an internal standard material, it showed 98% or higher. |
Here is a chemical reaction formula: Reactants are m3:FC1=C(C(=C(C(=C1B(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.C1(=CC=CC=C1)C, amount is: 0.0 MOLE;m1_m4_m2:FC=1C(=C(C(=C(C1)F)F)F)F, amount is: 0.0 ;m1_m4_m2:C(C)(CC)[Li].CCCCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C(C(=C(C(=C1[B-](C1=C(C(=C(C(=C1F)F)F)F)F)(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.[Li+], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of pentafluorobenzene (4.40 g, 26.2 mmol) and diethyl ether (50 ml) was added dropwise a 20 wt. % sec-butyllithium/hexane solution (7.98 g, 25.0 mmol) while keeping the temperature of the reaction mixture at -55° to -65° C., and, after the completion of dropwise addition, the mixture was stirred for about 0.5 hours while keeping the temperature at -25°-50° C. Thereafter, a 20.0 wt. % tris(pentafluorophenyl)borane/toluene solution (63.8 g, 25.0 mmol was mixed while keeping the temperature of the reaction mixture at -25° to -40° C., which was stirred for 30 minutes at the same temperature and then the temperature was raised to room temperature. From the solution of lithium tetrakis(pentafluorophenyl)borate thus obtained, diethyl ether was removed by distillation and the organic layer was washed thrice with 20 mL of water. After combining the aqueous layers, 1.1 equivalent to the boron source of an aqueous solution of N,N-dimethylanilinium chloride was reacted with the aqueous layer to deposit white crystals. The crystals obtained were filtered, washed with water and then dried under vacuum to obtain N,N-dimethuylanilinium tetrakis(pentafluorophenyl)borate in 96.1% yield. When determining the purity by means of 1H and 19F NMR using pentafluorotoluene as an internal standard material, it showed 98% or higher. |
Here is a chemical reaction formula: Reactants are m1:FC=1C=CC=C(C1F)F, amount is: 0.0 MOLE;m2:CCOC(=O)C1CCC(=O)CC1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m3:Cl[Ti](OC(C)C)(OC(C)C)OC(C)C, amount is: 0.0 MOLE.Products are 0:OC1(CCC(CC1)C(=O)OCC)C1=CC(=C(C(=C1)F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Thus, 1-triisopropyloxytitanyl, 3,4,5-trifluorobenzene--prepared by transmetalation of 3,4,5-trifluorobenzenemagnesiumbromide using chlorotriisopropyloxytitanium--is reacted chemoselectively with ethyl cyclohexanone-4-carboxylate (1) on the carbonyl group to give ethyl 4-hydroxy-4(3,4,5-trifluorophenyl)cyclohexanecarboxylate. Elimination of water, catalytic hydrogenation over Pd/C, hydrolysis and epimerization using KOH/methanol give the pure trans 4-(3,4,5-trifluorophenyl)cyclohexanecarboxylic acid-(1). The latter is converted into the mixed anhydride using pivaloyl chloride and, using N,O-dimethylhydroxylamine, into the corresponding amide. The latter is reduced in high yield using LiAlH4 to give the aldehyde IIIa'. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FCCCC(CO)CO, amount is: 0.0 MOLE;m1_m2_m3_m4:FC=1C=C(C=CC1F)C1=CC=C(C=O)C=C1, amount is: 0.0 MOLE;m1_m2_m3_m4:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ;m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC=1C=C(C=CC1F)C1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)CCCF, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 0.1 m of 2-(3-fluoropropyl)-1,3-propanediol, 0.1 m of p-(3,4-difluorophenyl)benzaldehyde (prepared by cross-coupling as described above), 1 g of p-toluenesulfonic acid and 200 ml of toluene is boiled for 1 hour on a water separator. Extractive work-up and purification by crystallization and chromatography give trans-2-(3,4-difluorobiphenyl-4'-yl)-5-(3-fluoropropyl)-1,3-dioxane. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:FC1=C(C=CC=C1)O, amount is: 0.0 ;m1_m2_m3_m5:S(=O)(=O)(O[C@H](CCCCC)C)C1=CC=C(C)C=C1, amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CCC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C[C@H](CCCCC)OC1=C(C=CC=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A reaction vessel was charged with 10 g of 2-fluorophenol, 25 g of (S)-1-methylhexyl tosylate, 20 g of potassium carbonate and 160 ml of MEK, and the mixture was refluxed with stirring for 14 hours (the disappearance of the starting materials was confirmed by TLC). The reaction liquid was poured into diluted hydrochloric acid and the mixture was extracted with benzene. The extract was washed with water and dried over Glauber's salt, and the solvents were distilled off. The residue was distilled under reduced pressure to obtain 14 g (74.5%) of (R) -2- (1-methylhexyl) oxyfluorobenzene. |
Here is a chemical reaction formula: Reactants are m2:C(C)(=O)Cl, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE;m3_m5:BrC1=CC(=C(C=C1)C1=CC=CC=C1)F, amount is: 0.0 ;m1_m6:[Cl-].[Al+3].[Cl-].[Cl-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:C(Cl)Cl, amount is: 0.0 ;m1_m6:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)C1=CC=C(C=C1)C1=C(C=C(C=C1)Br)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A reaction vessel was charged with 113 g of anhydrous aluminum chloride and 600 ml of methylene chloride. To the mixture was added dropwise 113 g of acetyl chloride with stirring at a temperature not higher than 0° C., and was then added dropwise a solution of 100 g of 4-bromo-2-fluoro-biphenyl in 400 ml of methylene chloride. The mixture was reacted with stirring for 7 hours while gradually bringing it back to room temperature. The reaction liquid was poured into ice and diluted hydrochloric acid. The methylene chloride layer was washed successively with water, an aqueous solution of sodium hydrogen carbonate and water, and then dried over Glauber's salt. The solvent was then distilled off and the residue was recrystallized from acetone to give 96 g (82.2%) of 4-acetyl-2'-fluoro-4'-bromobiphenyl. |
Here is a chemical reaction formula: Reactants are m1_m3:COC=1C=C(CN2[C@@H]([C@@H](C2=O)NC(=O)OCC2=CC=CC=C2)[C@H](CO)O)C=CC1OC, amount is: 0.0 ;m2:C(=O)(N1C=NC=C1)N1C=NC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=C(CN2[C@@H]([C@@H](C2=O)NC(=O)OCC2=CC=CC=C2)[C@H]2OC(OC2)=O)C=CC1OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 215.23 g (0.5 mol) of benzyl (2S,3S)-1-(3,4-dimethoxybenzyl)-2-[1(R),2-dihydroxyethyl]-4-oxo-3-azetidinecarbamate were dissolved In 3 l of THF at the boiling temperature. 12.61 g (0.75 mol) of 1,1'-carbonyldiimidazole were added. The mixture was boiled under reflux for 4 hours. The THF was subsequently removed by concentration, the oily residue was taken up in 1.5 l of dichloromethane, washed once with 500 ml of 1N aqueous hydrochloric acid, twice with 1 l of water each time and once with 500 ml of saturated, aqueous sodium chloride solution and dried over magnesium sulphate with the addition of about 7 g of fuller's earth. The solvent was removed by concentration. After drying there were obtained without further purification 220.3 g (yield: 96%) of pure product. M.p.: 135°-136° C. |
Here is a chemical reaction formula: Reactants are m3:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m2:C1=CN=CC=C1SC2=CC=NC=C2, amount is: 0.0 ;m1:ClC1=CC=CC(=C1C(=O)O)OC1=NC(=CC(=N1)OC)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1=CC=C(C=C1)SOC(C1=C(C=CC=C1Cl)OC1=NC(=CC(=N1)OC)OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 31.0 g of 6-chloro-2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid, 22.0 g of 4,4'-dipyridylsulfide and 26.2 g of triphenylphosphine were suspended in 250 ml of toluene, and were violently stirred at room temperature for 2 hours. The reaction mixture was filtered, and the toluene was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography to obtain 36.0 g of the above identified compound as a white crystal (yield 90%). |
Here is a chemical reaction formula: Reactants are m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m2:Cl.NO, amount is: 0.0 ;m1:C(C1=CC=CC=C1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)=NO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 10.6 g of benzaldehyde, 7.0 g of hydroxylamine HCl salt and 14.0 g of potassium carbonate were suspended in 200 ml of methanol, and were stirred at room temperature for 5 hours. The reaction mixture was filtered, and the methanol was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography to obtain 12.0 g of the above identified compound as a white crystal (yield 99%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C)OC(=O)NC(=S)NC=1C(=NC=CC1)C(=O)OC, amount is: 0.0 ;m1_m2_m3_m4:C[O-].[Na+], amount is: 0.0 ;m1_m2_m3_m4:CO, amount is: 0.14000000059604645 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC=1C2=C(N=C(N1)S)C=CC=N2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 37.2 g (0.13 mol) of N-ethoxycarbonyl-N'-(2-methoxycarbonyl-3-pyridinyl)thiourea and 33 mL of 25 percent sodium methoxide in methanol (0.14 mol) in 500 mL of absolute ethanol was heated to reflux with stirring. A solid began to form after about 5 min and after 1 hour heating was discontinued and the volatile components were removed by evaporation under reduced pressure. The residue was diluted with water, acidified with acetic acid, and filtered to recover the solids. The solids were extracted on the filter with ether and then with acetone to obtain a fine powder that was difficult to filter. This was extracted with ether again (added while some acetone was still present) and, finally, with hexane to obtain the 23.3 g of title compound as a more easily filtered pale yellow granular solid melting above 300° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:OC=1C2=C(N=C(N1)SC)C=CC=N2, amount is: 0.0 ;m1_m2_m3:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ;m1_m2_m3:C(C)#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C2=C(N=C(N1)SC)C=CC=N2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 19.0 g (98 mmol) of 4-hydroxy-2-methylthiopyrido[3,2-d]pyrimidine, 36.5 mL (60 g, 390 mmol) of phosphorus oxychloride and 200 mL of acetonitrile was prepared and heated to reflux with stirring. Since not much appeared to happen, about 1 mL of N,N-dimethylformamide was added. The solids then all went into solution in about 10 min. After about 2 hours, the volatiles were removed by evaporation under reduced pressure and the residue was diluted with dichloromethane. The resulting mixture was carefully washed with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was diluted with hexane and the solids were recovered by filtration and dried to obtain 17.8 g of the title compound melting at 120°-121° C. |
Here is a chemical reaction formula: Reactants are m2_m3:ClC=1C2=C(N=C(N1)SC)C=CC=N2, amount is: 0.0 ;m1:O.NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(N)C=1C2=C(N=C(N1)SC)C=CC=N2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Hydrazine hydrate (13.0 mL (13.3 g, 237 mmol)) was added at ambient temperature with stirring to a mixture of 16.7 g (79 mmol) of 4-chloro-2-methylthiopyrido[3,2-d]pyrimidine in 200 mL of ethanol. There was a slight exotherm and the mixture thickened and then became more mobile again. After 30 min, the volatile components were removed by evaporation under reduced pressure. The residue was diluted with water and the solids were recovered by filtration, washed with ether, and dried to obtain 15.7 g of the title compound as a brown powder melting above 300° C. |
Here is a chemical reaction formula: Reactants are m2:C(=S)=S, amount is: 0.0 ;m4_m6:C(C1=CC=CC=C1)Cl, amount is: 0.0 ;m1:N(N)C=1C2=C(N=C(N1)SC)C=CC=N2, amount is: 0.0 ;m3:C(C1=CC=CC=C1)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:CCOCC, amount is: 0.0 MOLE;m4_m6:C(C)N(CC)CC, amount is: 0.0 ;m8:O1CCOCC1, amount is: 0.0 ;m7:O1CCOCC1, amount is: 0.0 ;m9:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)SC1=NN=C2N1C(=NC1=C2C=CC=N1)SC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Hydrazino-2-methylthiopyrido[3,2-d]pyrimidine (14.5 g, 70 mmol) was combined with 200 mL of dioxane, 12.6 mL (16.0 g, 210 mmol) of carbon disulfide, and 29 mL (21.2 g, 210 mmol) of triethylamine and the mixture was heated at reflux with stirring for 4 hours during which time another 50 mL of dioxane was added to facilitate stirring. The mixture was allowed to cool, 13.3 g (105 mmol) of benzyl chloride was added, and the resulting mixture was allowed to stir overnight. Another 6 g of benzyl chloride and 25 mL of triethylamine were added and the mixture was heated to reflux with stirring for a short period. The volatile components were removed by evaporation under reduced pressure and the residue was diluted with dichloromethane and water. The resultant emulsion was filtered to obtain separable phases and the organic phase was washed with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was diluted with hexane and the resulting black solid was recovered by filtration. This solid was diluted with dichloromethane and the solution obtained was filtered through silica gel. Evaporation of the filtrate under reduced pressure gave a black solid that was diluted with ether and recovered by filtration to obtain 18.8 g the title compound melting at 157°-158° C. The proton NMR spectrum was compatible with the assigned structure. Work up of the filtrate gave an additional 6 g of impure title compound as a black oil. |
Here is a chemical reaction formula: Reactants are m2_m3_m6:C(C=C)(=O)OCC, amount is: 0.0 ;m2_m3_m6:C[O-].[Na+], amount is: 0.0 ;m1_m5:C(C1=CC=CC=C1)SC1=NN=C2N1C(=NC1=C2C=CC=N1)SC, amount is: 0.0 ;m4:C(C)(=O)O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3_m6:CO, amount is: 10.0 MILLIMOLE;m1_m5:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)SC1=NN2C(=NC3=C(C2=N1)C=CC=N3)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 17.7 g (52 mmol) of 3-benzylthio-5-methylthiopyrido[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine in 200 mL of methanol was prepared and to this was added at ambient temperature with stirring 8.5 mL (7.8 g, 78 mmol) of ethyl acrylate and 2.4 mL of 25 percent sodium methoxide in methanol (10 mmol). Everything dissolved fairly quickly and after 15 min new precipitate formed. After about 1 hour the mixture was acidified with acetic acid and the volatile components were removed by evaporation under reduced pressure. The residue was dissolved in dichloromethane and the resulting solution was washed with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was diluted with ether, recovered by filtration, and dried to obtain 14.6 g of the title compound as a brown powder melting at 282°-284° C. with decomposition. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:ClS(=O)(=O)C1=NN2C(=NC3=C(C2=N1)C=CC=N3)OC, amount is: 0.0 ;m1_m2_m3_m5:ClC1=C(N)C(=CC=C1)Cl, amount is: 0.0 ;m1_m2_m3_m5:N1=CC=CC=C1, amount is: 0.0 ;m4:CS(=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C(=CC=C1)Cl)NS(=O)(=O)C1=NN2C(=NC3=C(C2=N1)C=CC=N3)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2.0 g (6.7 mmol) of 2-chlorosulfonyl-5-methoxypyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine, 2.2 g (13.3 mmol) of 2,6-dichloroaniline, 0.50 g (67 mmol) of pyridine, and 30 mL of dry acetonitrile was prepared and to this was added with stirring at ambient temperature 95 microliters (1.3mmol) of dimethyl sulfoxide. The mixture was allowed to react overnight and was then concentrated by evaporation under reduced pressure. The residue was diluted with dichloromethane and water and the resulting mixture was filtered to remove the insoluble solids. The organic phase was recovered and the dichloromethane was removed by evaporation under reduced pressure. The residue was diluted with hexane, recovered by filtration, and redissolved in dichloromethane. The resulting solution was filtered through silica gel and concentrated by evaporation under reduced pressure. The residue was diluted with hexane, recovered by filtration, and dried to obtain 0.25 g of the title compound as a light tan powder melting at 290°-293° C. with decomposition. The proton NMR spectrum of this was compatible with the assigned structure. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:NC1=C(SC=C1)C(=O)OC, amount is: 0.0 MOLE;m1_m4_m2:C(C)OC(=O)N=C=S, amount is: 0.0 ;m3:CCCCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C(Cl)(Cl)Cl, amount is: 0.0 ;m5:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OC(=O)NC(=S)NC1=C(SC=C1)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 3-amino-2-thiophenecarboxylate (5.0 g (32 mmol) was dissolved in 16 mL of chloroform and to this solution 4.17 g (32 mmol) of ethoxycarbonyl isothiocyanate was added slowly with stirring at ambient temperature. A precipitate began to appear after a few minutes and after 20 min the volatile components were removed by evaporation under reduced pressure. The tan solid residue obtained was diluted with 20 mL of ether and allowed to stir for about 20 min and then 100 mL of hexane was added. The insoluble solids were recovered by filtration and dried to obtain 8.51 g of the title compound as a tan solid melting at 165°-167° C. |
Here is a chemical reaction formula: Reactants are m2:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ;m3:CN(C1=CC=CC=C1)C, amount is: 0.0 ;m1:OC=1C2=C(N=C(N1)SC)C=CS2, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)#N, amount is: 0.0 ;m4:C(C)#N, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C2=C(N=C(N1)SC)C=CS2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Hydroxy-2-methylthiothiopheno[3,2-d ]pyrimidine (15.4 g, 78 mmol) was combined with 50 mL of dry acetonitrile and 29 mL (312 mmol) of phosphoryl chloride and 10 mL (78 mmol) of N,N-dimethylaniline were added with stirring. The mixture was heated to reflux with stirring for 2 hours. It was then allowed to cool and most of the acetonitrile was removed by evaporation under reduced pressure. The residue was poured slowly into 200 mL of cold water with cooling and agitation. The resulting mixture was extracted with 4×500 mL of ether and the combined ethereal extracts were dried over magnesium sulfate and concentrated by evaporation under reduced pressure. The 15.3 g of tan solid title compound obtained melted at 115°-118° C. and had a proton NMR spectrum consistent with the assigned structure. |
Here is a chemical reaction formula: Reactants are m4_m5:ClCCl, amount is: 0.0 ;m1_m2:ClC=1C2=C(N=C(N1)SC)C=CS2, amount is: 0.0 ;m1_m2:C(C)O, amount is: 0.0 ;m3:O.NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(N)C=1C2=C(N=C(N1)SC)C=CS2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Chloro-2-methylthiothiopheno[3,2-d]pyrimidine (15.26 g, 70.4 mmol) was mixed with 400 mL of ethanol and then 7.2 mL (148 mmol) of hydrazine hydrate was added with stirring at ambient temperature and the mixture was allowed to stir overnight. The solid materials present were recovered by filtration and the filtrate was evaporated to dryness under reduced pressure to obtain additional solid material. All of the solids were combined and mixed vigorously with a mixture of 500 mL of dichloromethane and 500 mL of water for 6 hours. The solids present were recovered by filtration and dried to obtain 13.9 g of the title compound as a slightly yellow solid melting at 242°-244° C. The proton NMR spectrum was consistent with the assigned structure. |
Here is a chemical reaction formula: Reactants are m6:C(C)(=O)O, amount is: 0.0 MOLE;m2_m3_m7:C(C=C)(=O)OC, amount is: 0.0 ;m2_m3_m7:C[O-].[Na+], amount is: 0.0 ;m4_m8:C[O-].[Na+], amount is: 0.0 ;m1_m11:C(C1=CC=CC=C1)SC1=NN=C2N1C(=NC1=C2C=CS1)SC, amount is: 0.0 MOLE;m5_m9:C[O-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3_m7:CO, amount is: 0.0 MOLE;m4_m8:CO, amount is: 0.0 MOLE;m1_m11:CO, amount is: 0.0 ;m5_m9:CO, amount is: 0.0 MOLE;m10:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)SC1=NN2C(=NC3=C(C2=N1)C=CS3)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-Benzylthio-5-methylthiothieno[3,2-e][1,2,4]-triazolo[4,3-c]pyrimidine (19.2 g (57.2 mmol)was mixed with 100 mL of methanol and to this was added with stirring 7.7 mL (86 mmol) of methyl acrylate and 3.3 mL of 25 percent sodium methoxide in methanol. After 2 hours at ambient temperature, the mixture was heated to reflux for about 2.5 hours during which time another 10 mL of 25 percent sodium methoxide in methanol was added. The mixture was stirred at ambient temperature overnight and then another 5 mL of the 25 percent sodium methoxide in methanol was added and the mixture heated to reflux again for 2 hours. The resulting mixture was acidified with acetic acid and was then concentrated by evaporation under reduced pressure to obtain a tan solid. This was dissolved in 600 mL of dichloromethane and the solution obtained was washed 3×100 mL with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The tan, solid residue was flash chromatographed on silica gel (240-400 mesh, 5×20 cm (centimeter) column) eluting with mixtures of hexane and ethyl acetate ranging from 90:10 to 50:50. The second compound to elute was collected to obtain 12.6 g of the title compound as a nearly white solid melting at 160°-162° C. The proton NMR spectra of this was consistent with the assigned structure. |
Here is a chemical reaction formula: Reactants are m1_m2_m5:ClS(=O)(=O)C1=NN2C(=NC3=C(C2=N1)C=CS3)OC, amount is: 0.0 ;m1_m2_m5:ClC1=C(N)C(=CC=C1)Cl, amount is: 0.0 ;m3_m4:N1=CC=CC=C1, amount is: 0.0 ;m3_m4:CS(=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C(=CC=C1)Cl)NS(=O)(=O)C1=NN2C(=NC3=C(C2=N1)C=CS3)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chlorosulfonyl-5-methoxythieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (1.5 g, 4.9 mmol) and 2,6-dichloroaniline (1.59 g, 9.8 mmol) were dissolved in 20 mL of acetonitrile and to this was added under nitrogen at ambient temperature with stirring 0.40 mL (4.9 mmol) of pyridine and 0.05 mL of dimethyl sulfoxide. The mixture was allowed to stir overnight and was then concentrated by evaporation under reduced pressure. The residue was flash chromatographed on silica gel and fractions containing the major product were recovered. Evaporation of the solvents under reduced pressure gave a white powder. This was extracted with 200 mL of hexane and the insoluble white solid was dried to obtain 1.0 g of the title compound melting at 224°-226° C. The proton NMR spectra of this was consistent with the assigned structure. |
Here is a chemical reaction formula: Reactants are m3:[H][H], amount is: 0.0 MOLE;m1_m4_m2_m5:FC1=NC=CC(=C1[N+](=O)[O-])C, amount is: 0.0 ;m1_m4_m2_m5:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m5:C(C)(=O)OCC, amount is: 0.0 ,Catalysts are m1_m4_m2_m5:[Pd], amount is: 0.0 .Products are 0:NC=1C(=NC=CC1C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 10.1 g (65 mmol) of 2-fluoro-4-methyl-3-nitropyridine in 200 mL of ethyl acetate was added 25 g (0.40 mol) of acetic acid and 0.8 g of 5 percent palladium on carbon catalyst. This mixture was shaken under 50 psig (pounds per square inch gauge) (2400 kiloPascals) pressure of hydrogen for 18 hours, was filtered, and was concentrated by evaporation under reduced pressure to obtain an oil. This oil was partitioned between dilute aqueous sodium bicarbonate and ether. The organic phase was recovered, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography to obtain 7.2 g (88 percent of theory) of the title compound as a colorless solid melting at 63°-64° C. Nuclear Magnetic Resonance Spectrum (200 MHz (megaHertz), CDCl3): 1H: 7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.1 (s, 3H); 13C: 152.6 (d, J=229); 134.1 (d, J=8.6); 133.8 (d, J=14.5); 128.1 (d, J=27.1); 123.3, 16.4 (d, J=4.1). |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 ;m2:OO, amount is: 0.0 ;m3:C([O-])(O)=O.[Na+], amount is: 0.0 ;m1:NC=1C=NC=CC1OC, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:NC=1C(=NC=CC1OC)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 6.4 g (51 mmol) of 3-amino-4-methoxypyridine in 30 mL of 37 percent aqueous hydrochloric acid was slowly added 7.8 g of 30 percent aqueous hydrogen peroxide at room temperature with stirring. After 30 min this solution was slowly poured into 300 mL of saturated aqueous sodium bicarbonate and the resulting mixture was extracted with ether (3×200 mL). The ethereal extracts were combined, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure to obtain a light brown solid. This solid was purified by column chromatography (17:83 acetone:hexane) to obtain 6.54 g (81 percent of theory) of the title compound as colorless needles melting at 86°-87° C. |
Here is a chemical reaction formula: Reactants are m3:[H][H], amount is: 0.0 MOLE;m1_m6_m2:O[C@@H]1C[C@H](NC1)C(=O)O, amount is: 0.0 ;m1_m6_m2:C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m5:O, amount is: 0.0 ;m1_m6_m2:CO, amount is: 0.0 ,Catalysts are m4_m5:[Pd], amount is: 0.0 MOLE.Products are 0:CN1[C@H](C(=O)O)C[C@H](C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 10% palladium on carbon in water (25 ml) was added to a suspension of trans-4-hydroxy-L-proline (6.576 g., 50.10 mmol) in methanol (100 ml) and 37% aqueous formaldehyde (16 ml, 213.5 mmol) in a Parr bottle. The bottle was pressurized to 50 psi with hydrogen and shaken overnight. The catalyst was removed by filtration through a pad of celite which was washed thoroughly with methanol (100 ml). Evaporation of the methanol and excess formaldehyde yielded N-methyl-trans-4-hydroxy-L-proline as a white solid which was recrystallized from methanol/diethyl ether to give 6.425 g. of white needles, m.p. 236°-238 ° (decomposition with gas evolution). |
Here is a chemical reaction formula: Reactants are m3:C1(=CC=CC=C1)S, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE;m1_m2_m5:C1(=CC=C(C=C1)S(=O)(=O)OC[C@@H](C)C1(CCCC1)O)C, amount is: 0.0 ;m1_m2_m5:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=C(C=C1)S(=O)(=O)OC[C@H](C)C1(CCCC1)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 4a (3.65 g, 11.9 mmol) and triethylamine (2.5 mL) in N, N-dimethylformamide (18 mL) was added thiophenol (1.8 mL) in one portion. The mixture was stirred at ambient temperature overnight. The mixture was poured into water, and extracted with diethyl ether. The combined organic layers were washed with sodium bicarbonate solution and brine, and dried over sodium sulfate. Filtration and concentration gave 3.26 g of an oily material, which was purified by column chromatography (silica gel 40 g, ethyl acetate in n-hexane, 2.5-20%) to give 2.06 g (73.3%) of 5a, as a pale yellow oil. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 MOLE;m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m5:C(CCC)NC, amount is: 0.0 ;m1_m2_m5:ClCCCCCS(=O)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCC)N(S(=O)(=O)CCCCCCl)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.47 ml of N-butylmethylamine were added under an inert gas atmosphere to a solution of 410 mg of 5-chloropentane sulfonyl chloride in 10 ml of methylene chloride. The temperature rose from 13° C. to 26° C., and then after cooling to 0 to 5° C., 0.55 ml of triethylamine were added. The mixture was stirred at ambient temperature for 2 hours and the reaction medium was poured into an aqueous solution of 1M hydrochloric acid, extracted with methylene chloride, washed with water, then with a saturated aqueous solution of sodium chloride, dried and evaporated to dryness under reduced pressure to obtain 486 mg of the expected product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[I-].[Na+], amount is: 0.0 ;m1_m2_m3:C(CCC)N(S(=O)(=O)CCCCCCl)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)C(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCC)N(S(=O)(=O)CCCCCI)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 526 mg of sodium iodide were added to a solution of 449 mg of the product of Step A in 4.5 ml of methyl ethyl ketone, and the mixture was stirred at reflux for 4 hours. After cooling, the methyl ethyl ketone was evaporated under reduced pressure and water was added. Extraction was carried out with ethyl acetate and the extracts were washed with water, then with a saturated aqueous solution of sodium chloride, dried and evaporated to dryness under reduced pressure to obtain 572 mg of the expected product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:Cl.FC(CNC)(C(C(F)(F)F)(F)F)F, amount is: 0.0 ;m1_m2_m3_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m3_m5:ClCCCCCS(=O)(=O)Cl, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCCCCCS(=O)(=O)N(C)CC(C(C(F)(F)F)(F)F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 500 mg of N-(2,2,3,3,4,4,4-heptafluorobutyl)-N-methylamine hydrochloride (obtained according to European Patent No. 384,842 Example 75) and then, at 0° to 5° C., 0.55 ml of triethylamine were added to a solution of 200 mg of 5-chloropentane sulfonyl chloride in 5 ml of methylene chloride, and the mixture was stirred at ambient temperature for 2 hours. Water was added and extraction was carried out with methylene chloride. The extracts were washed with water, then with a saturated aqueous solution of sodium chloride, dried and evaporated to dryness under reduced pressure to obtain 378 mg of the expected product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[I-].[Na+], amount is: 0.0 ;m1_m2_m3:ClCCCCCS(=O)(=O)N(C)CC(C(C(F)(F)F)(F)F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)C(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(CN(S(=O)(=O)CCCCCI)C)(C(C(F)(F)F)(F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 300 mg of sodium iodide were added to a solution of 355 mg of the product of Step A in 3 ml of methyl ethyl ketone and the mixture was refluxed for 4 hours. After evaporation of the solvent, the residue was taken up in water and extracted with ethyl acetate. The extracts were washed with an aqueous solution of sodium thiosulfate, then of sodium chloride, and evaporated to dryness under reduced pressure to obtain 425 mg of the expected product in the form of a colourless oil which slowly crystallized. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:CC1=C(C=NO1)C(=O)Cl, amount is: 0.0 ;m1_m3_m2_m4:FC(C1=CC=C(N)C=C1)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:C(C)#N, amount is: 0.0 ;m1_m3_m2_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C=NO1)C(=O)NC2=CC=C(C=C2)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.05 mol of 5-methylisoxazole-4-carbonyl chloride (7.3 g) in 20 ml of acetonitrile is added dropwise at room temperature to a solution of 0.1 mol of 4-trifluoromethylaniline (16.1 g) in 150 ml of acetonitrile. After stirring for 20 minutes, the precipitated 4-trifluoromethylaniline hydrochloride is filtered off with suction and washed twice with 20 ml of acetonitrile each time and the combined filtrates are concentrated under reduced pressure. 12.8 g of white crystalline 5-methylisoxazole-4-carboxylic acid (4-trifluoromethyl)-anilide (compound 1) are thus obtained. |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 MOLE;m2_m5:[OH-].[Na+], amount is: 0.0 ;m1_m4:FC(OC1=CC=C(C=C1)NC(=O)C=1C=NOC1C)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 MOLE;m2_m5:O, amount is: 0.0 ;m1_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(OC1=CC=C(C=C1)NC(\C(=C(\C)/O)\C#N)=O)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.1 mol (28.6 g) of N-(4-trifluoromethoxyphenyl)-5-methylisoxazole-4-carboxamide is dissolved in 100 ml of ethanol and a solution of 0.11 mol (4.4 g) of sodium hydroxide solution in 100 ml of water is added at 20° C. The mixture is stirred for 30 minutes and acidified with concentrated hydrochloric acid after diluting with water. The precipitated crystal magma is filtered off with suction, washed with water and dried in the air. 27.7 g (9.1% of theory) of N-(4-trifluoromethoxyphenyl)-2-cyano-3-hydroxycrotonamide of melting point 171°-176° C. (from ethanol) are thus obtained. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:BrC=1C=CC2=C(C(CO2)=O)C1, amount is: 0.0 ;m1_m2_m4:C(#N)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m3:[PH5], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C=1(C(=CC=CC1)C)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=CC2=C(C(=CO2)CC#N)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 5-bromo-3-(2H)-benzofuranone (4.26 g) and cyanomethylene triphenylphosphorane (9.06 g) in dry xylene (100 ml) was heated at reflux for 24 h . A further quantity of the phosphorane (450 mg) was added and heating continued for a further period of 12 h. On cooling to ambient temperature the brown coloured suspension was evaporated to dryness in vacuo. Chromatography of the residue using dichloromethane:hexane (1:3) as eluant afforded a cream coloured product. Recrystallization (from ethanol) of the chromatographed material afforded the title compound as cream flakes, m.p. 120°. |
Here is a chemical reaction formula: Reactants are m1_m2_m5:CN(C(CP(OC)(OC)=O)=O)C, amount is: 0.0 ;m1_m2_m5:[H-].[Na+], amount is: 0.0 MOLE;m4:O, amount is: 0.0 ;m3_m6:BrC=1C=CC2=C(C(CO2)=O)C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:C1CCOC1, amount is: 0.0 ;m3_m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC1=CC2=C(OC(=C2)CC(=O)N(C)C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dimethyl [2-(dimethylamino)-2-oxoethyl]phosphonate (5 g) was added to a stirred suspension of sodium hydride (1.02 g of a 60% dispersion in oil) in dry THF (100 ml) at 0° under nitrogen. After stirring for 15 minutes 5-bromo-3-(2H)-benzofuranone (5.0 g) in THF (20 ml) was added dropwise and stirred at room temperature for 3 h. Water (50 ml) was added and the mixture extracted with ethyl acetate (3×50 ml), dried and the solvent removed in vacuo. The crude material was purified by flash chromatography using 50% ethyl acetate/hexane as eluant to yield the title compound as a pale yellow solid m.p. 92°-94° C. |
Here is a chemical reaction formula: Reactants are m1_m4:FC(P(OCC)(=O)OCC)F, amount is: 0.0 ;m2:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 ;m3:BrC1(C(C=CC=C1)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C=CC=C1)CC(F)(F)P(OCC)(OCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 30 mmol (5.64 g) of diethyl difluoromethane phosphonate dissolved in 30 ml of anhydrous tetrahydrofuran (THF) are slowly added to a stirred solution of (LDA) lithium diisopropylamide (prepared at 0° C. from 31 mmol of n-butyllithium and 30 mmol of diisopropylamine in 30 ml of anhydrous THF) at -78° C. under argon. After 30 minutes, 45 mmol (8.33 g) of 2-bromo-o-xylene are added to the reaction mixture which is stirred at -78° C. for 15 hours and quenched by adding 20 ml of an aqueous saturated solution of ammonium chloride. The crude mixture is evaporated to dryness; the residue is suspended in 50 ml of water and extracted 3 times with 100 ml of ethylacetate. The organic layers are dried over sodium sulfate, filtered and evaporated to give approximately 8 g of crude product which is purified by flash chromotography on silica gel affording 3.6 g of 1A (41% yield). |
Here is a chemical reaction formula: Reactants are m1_m2:ClC1=NOC2=C1C=CC(=C2)OC, amount is: 0.0 ;m1_m2:CNCCN1CCOCC1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:COC1=CC2=C(C(=NO2)N(CCN2CCOCC2)C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a sealed tube was added 3-chloro-6-methoxy-1,2-benzisoxazole (6.0 g) and N-methyl-N-[2-(4-morpholinyl)ethyl]-amine (13.8 g). The reaction was heated to 140° C. over 48 hours and then cooled to room temperature. The residue was partitioned between ethyl acetate (EtOAc) and water, extracted again with EtOAc, and the organic phase was dried over magnesium sulfate (MgSO4) and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 1% methanol/dichloromethane (MeOH/DCM) provided the product (4.7 g), m.p. 43°-44° C. |
Here is a chemical reaction formula: Reactants are m2:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 MOLE;m1_m3:COC1=CC2=C(C(=NO2)N(CCN2CCOCC2)C)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:Br, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(CCOCC1)CCN(C1=NOC2=C1C=CC(=C2)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6-Methoxy-N-methyl-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amine (7.0 g) was dissolved in 48% hydrobromic acid (130 ml) and heated to reflux under nitrogen for 3 hours. The reaction was cooled to room temperature, neutralized with saturated sodium carbonate (Na2CO3) extracted with ethyl acetate, dried over MgSO4 and concentrated in vacuo. Flash chromatography (silica gel) eluting with 2:1 heptane/acetone provided the product (6.0 g), m.p. 91°-92° C. |
Here is a chemical reaction formula: Reactants are m3:CO.C(Cl)Cl, amount is: 0.0 MOLE;m1_m5_m4_m2:N1(CCOCC1)CCN(C1=NOC2=C1C=CC(=C2)O)C, amount is: 0.0 ;m1_m5_m4_m2:CN=C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m4_m2:CCOC(=O)C, amount is: 0.0 ,Catalysts are m1_m5_m4_m2:[Cu]Cl, amount is: 0.0 .Products are 0:CNC(OC1=CC2=C(C(=NO2)N(C)CCN2CCOCC2)C=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol (2 g) and copper(I)chloride (0.3 g) in EtOAc (60 ml) was added methyl isocyanate (0.5 g). After 3.5 hours thin layer chromatography (TLC) (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (2 l) and the filtrate was concentrated in vacuo to yield 1.2 g of the product, m.p. 94°-95° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:N1(CCOCC1)CCN(C1=NOC2=C1C=CC(=C2)O)C, amount is: 0.0 ;m1_m2_m5_m3:N12CCCCCC2=NCCC1, amount is: 0.0 ;m1_m2_m5_m3:C1(=CC=CC=C1)CN=C=O, amount is: 0.0 ;m4:[N-]=C=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:CO.C(Cl)Cl, amount is: 0.0 MOLE;m1_m2_m5_m3:CCOC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)CNC(OC1=CC2=C(C(=NO2)N(C)CCN2CCOCC2)C=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol (2.3 g) and 1,8 diazabicyclo[5.4.0]undec-7-ene (0.2 g) in EtOAc (80 ml) was added phenylmethyl isocyanate (1.3 g). After 24 hours an additional equivalent of the isocyanate was added. TLC (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was concentrated in vacuo. Flash chromatography (silica gel) eluting with 1% MeOH/DCM provided the product (2.4 g), m.p. 106°-107° C. |
Here is a chemical reaction formula: Reactants are m3:CO.C(Cl)Cl, amount is: 0.0 MOLE;m1_m5_m4_m2:N1(CCOCC1)CCN(C1=NOC2=C1C=CC(=C2)O)C, amount is: 0.0 ;m1_m5_m4_m2:CC(C)N=C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m4_m2:CCOC(=O)C, amount is: 0.0 ,Catalysts are m1_m5_m4_m2:[Cu]Cl, amount is: 0.0 .Products are 0:CC(C)NC(OC1=CC2=C(C(=NO2)N(C)CCN2CCOCC2)C=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol (2.2 g) and copper(I)chloride (0.1 g) in EtOAc (50 ml) was added 1-methylethylisocyanate (0.8 g). After 24 hours TLC (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (3 l) and the filtrate was concentrated in vacuo. The white solid was flash chromatographed on silica gel eluting with 1% MeOH/DCM to yield 1.2 g of the product, m.p. 99°-100° C. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC1=NOC2=C1C=CC=C2, amount is: 0.0 ;m1_m2:CNCCN1CCOCC1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CN(C1=NOC2=C1C=CC=C2)CCN2CCOCC2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a sealed tube was added 3-chloro-1,2-benzisoxazole (3.0 g) and N-methyl-N-[2-(4-morpholinyl)ethyl]-amine (12.7 g). The reaction was heated to 140° C. over 72 hours and then cooled to room temperature. The residue was partitioned between EtOAc and water, extracted again with EtOAc, and the organic phase was dried over MgSO4 and concentrated in vacuo. Hash column chromatography (silica gel) eluting with 1-3% MeOH/DCM provided the product (1.2 g), as an oil. |
Here is a chemical reaction formula: Reactants are m4:CO.C(Cl)Cl, amount is: 0.0 MOLE;m1_m5_m2:NC1=NOC2=C1C=CC=C2, amount is: 0.0 ;m1_m5_m2:[H-].[Na+], amount is: 0.0 ;m3_m6:ClCCN1CCOCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:CN(C=O)C, amount is: 0.0 ;m3_m6:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(CCOCC1)CCNC1=NOC2=C1C=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-amino-1,2-benzisoxazole (3.5 g) in N,N-dimethylformamide (DMF) (100 ml) was added sodium hydride (0.8 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)morpholine (4.0 g) in DMF (50 ml) was added followed by heating to 120° C. for one hour. TLC (5% MeOH/DCM) analysis revealed the absence of starting material. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with water, dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 1.5-2.5% MeOH/DCM afforded the product (2.5 g), m.p. 79°-80° C. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m3:COC1=CC(=C(C#N)C=C1)[N+](=O)[O-], amount is: 0.0 ;m5_m1:CC(C)=NO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m1:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=CC(=C(C#N)C=C1)ON=C(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In 20 ml of DMF was dissolved acetone oxime (0.74 g), followed by sodium hydride (0.30 g). After this mixture had stirred for 30 minutes, 4-methoxy-2-nitro-benzonitrile (1.50 g) was added. After an additional 30 minutes the reaction was poured into water (500 ml) and filtered. The solid was collected and dissolved in DCM (250 ml), dried (MgSO4), and concentrated in vacuo. The resulting solid was recrystallized from ethanol to yield 1.5 g of 4-methoxy-2-[[(1-methylethylidene)amino]oxy]benzonitrile, m.p. 78°-79° C. |
Here is a chemical reaction formula: Reactants are m1_m5_m2:NC1=NOC2=C1C=CC(=C2)OC, amount is: 0.0 ;m1_m5_m2:[H-].[Na+], amount is: 0.0 ;m3_m6:ClCCN1CCOCC1, amount is: 0.0 ;m4:CO.C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2:CN(C=O)C, amount is: 0.0 ;m3_m6:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=CC2=C(C(=NO2)NCCN2CCOCC2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-amino-6-methoxy-1,2-benzisoxazole (5.5 g) in N,N-dimethylformamide (DMF) (100 ml) was added sodium hydride (1.2 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)morpholine (5.4 g) in DMF (50 ml) was added to the reaction and heated to 125° C. for one hour. TLC (5% MeOH/DCM) revealed the absence of starting material. The reaction was quenched with water (1 l) and extracted with EtOAc (2 l). The organic layer was washed with water, dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 3-4% MeOH/DCM afforded the product (4.5 g), m.p. 85°-86° C. |
Here is a chemical reaction formula: Reactants are m1_m3:COC=1C=CC2=C(C(=NO2)N(CCN2CCOCC2)C)C1, amount is: 0.0 ;m2:C(=O)([O-])[O-].[Na+].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:Br, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(CCOCC1)CCN(C1=NOC2=C1C=C(C=C2)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Methoxy-N-methyl-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amine (2.6 g) was dissolved in 48% hydrobromic acid (40 ml) and heated to reflux under nitrogen for 6 hours. The reaction was cooled to room temperature, neutralized with saturated Na2CO3 solution, and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo. Flash chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM provided the pure product (2.1 g), 153°-154° C. |
Here is a chemical reaction formula: Reactants are m3:CO.C(Cl)Cl, amount is: 0.0 MOLE;m1_m5_m4_m2:N1(CCOCC1)CCNC1=NOC2=C1C=CC(=C2)O, amount is: 0.0 ;m1_m5_m4_m2:CN=C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m4_m2:CCOC(=O)C, amount is: 0.0 ,Catalysts are m1_m5_m4_m2:[Cu]Cl, amount is: 0.0 .Products are 0:CNC(OC1=CC2=C(C(=NO2)NCCN2CCOCC2)C=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-ol (2 g) and copper(I)chloride (0.3 g) in EtOAc (60 ml) was added methyl isocyanate (0.5 g). After 3.5 hours TLC (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (2 l) and the filtrate was concentrated in vacuo. Flash column chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM afforded a white solid which was recrystallized from EtOAc/pet. ether to yield 0.7 g of the expected product, m.p. 127°-128° C. |
Here is a chemical reaction formula: Reactants are m3:CC(=O)C.CO.C(Cl)Cl, amount is: 0.0 MOLE;m1_m5_m4_m2:N1(CCOCC1)CCNC1=NOC2=C1C=C(C=C2)O, amount is: 0.0 ;m1_m5_m4_m2:CN=C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m4_m2:CCOC(=O)C, amount is: 0.0 ,Catalysts are m1_m5_m4_m2:[Cu]Cl, amount is: 0.0 .Products are 0:CNC(OC=1C=CC2=C(C(=NO2)NCCN2CCOCC2)C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-ol (1 g) and a catalytic amount of copper(I)chloride (0.05 g) in EtOAc (100 ml) was added methyl isocyanate (0.26 g). After 24 hours TLC (silica gel, 1:1:20 acetone/MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina during with EtOAc (1 l) and the filtrate was concentrated in vacuo. The residue was further purified by flash chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM to yield 0.4 g of the product, m.p. 135°-136° C. |
Here is a chemical reaction formula: Reactants are m2:[K], amount is: 0.0 ;m5_m1:CC(C)=NO, amount is: 0.0 ;m3:ClC1=CC(=C(C#N)C=C1)[N+](=O)[O-], amount is: 0.0 ;m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m1:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC(=C(C#N)C=C1)ON=C(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In 75 ml of dry N,N-dimethylformamide was dissolved acetone oxime (1.21 g), followed by potassium tertiaryl butoxide (1.85 g) and stirred under nitrogen. After 30 minutes, 4-chloro-2-nitro-benzonitrile (2.00 g) was added. After an additional 30 minutes the reaction was poured into water (500 ml) and filtered. The solid was collected and dissolved in DCM (250 ml), dried (MgSO4), and concentrated in vacuo. The resulting solid was recrystallized from ethanol to yield 1.5 g of the product, m.p. 83°-84° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:N1(CCOCC1)CCNC1=NOC2=C1C=CC(=C2)O, amount is: 0.0 ;m1_m2_m5_m3:N12CCCCCC2=NCCC1, amount is: 0.0 ;m1_m2_m5_m3:CN(C(=O)Cl)C, amount is: 0.0 ;m4:CO.C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m5_m3:ClCCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C(OC1=CC2=C(C(=NO2)NCCN2CCOCC2)C=C1)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-ol (Example 9) (1.5 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.13 g) in 1,2-dichloroethane (40 ml) was added dimethylcarbamyl chloride (0.65 g). The mixture was refluxed for 24 hours under N2. TLC (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was filtered and the filtrate concentrated in vacuo. Flash chromatography (silica gel) eluting with 5% acetone/5% MeOH/CH2Cl2 provided a residue which upon crystallization afforded 0.5 g of the product, m.p. 150° C. |
Here is a chemical reaction formula: Reactants are m1_m6_m2:C(C)(=O)NO, amount is: 0.0 ;m1_m6_m2:CC(C)([O-])C.[K+], amount is: 0.0 ;m3:FC1=C(C#N)C=CC(=C1)OCOC, amount is: 0.0 ;m4_m5_m8:C(C)(=O)NO, amount is: 0.0 MOLE;m4_m5_m8:C(C)(C)(C)O[K], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m9:CCOC(=O)C, amount is: 0.0 ;m7:CC(=O)C.C(Cl)(Cl)Cl, amount is: 0.0 MOLE;m1_m6_m2:CN(C=O)C, amount is: 0.0 ;m4_m5_m8:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=NOC2=C1C=CC(=C2)OCOC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of acetohydroxamic acid (3.88 g) in N,N-dimethylformamide (DMF) (120 ml) was added potassium tertiarybutoxide (tBuOK) (5.80 g) under N2. After one hour of stirring 2-fluoro-4-(methoxymethoxy)-benzonitrile (6.0 g) was added. Stirring continued for 16 hours. TLC (silica gel) in 10% acetone/CHCl3 showed the presence of starting material. An additional 1 equivalent of acetohydroxamic acid and tBuOK were added in DMF (120 ml). After one hour the reaction was diluted with EtOAc (2 l), filtered, washed filtrate with brine (4×11), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) was performed eluting with 2.5% acetone/CH2Cl2 solution affording 8.1 g of the product, m.p. 88°-89° C. |
Here is a chemical reaction formula: Reactants are m4:CO.C(Cl)Cl, amount is: 0.0 MOLE;m1_m5_m2:NC1=NOC2=C1C=CC(=C2)OCOC, amount is: 0.0 ;m1_m5_m2:[H-].[Na+], amount is: 0.0 ;m3_m6:ClCCN1CCSCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:CN(C=O)C, amount is: 0.0 ;m3_m6:CN(C=O)C, amount is: 0.0 ;m7:CCOC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COCOC1=CC2=C(C(=NO2)NCCN2CCSCC2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-amino-6-methoxymethoxy-1,2-benzisoxazole (4.0 g) in N,N-dimethylformamide (DMF) (50 ml) was added sodium hydride (0.74 g) under nitrogen. The reaction was stirred one hour at ambient temperature. A solution of 4-(2-chloroethyl)thiomorpholine (3.6 g) in DMF (25 ml) was added to the reaction and heated to 125° C. for three hours. TLC (5% MeOH/CH2Cl2) revealed the absence of starting material. The reaction was diluted with EtOAc (1 l), washed with brine (4×500 ml), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (silica gel) eluting with 5% acetone/CH2Cl2 afforded the the product (2.0 g). |
Here is a chemical reaction formula: Reactants are m4_m1:CC(C)=NO, amount is: 0.0 ;m2:CC(C)([O-])C.[K+], amount is: 0.0 ;m3:COC=1C=CC(=C(C#N)C1)[N+](=O)[O-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m1:CN(C)C=O, amount is: 0.0 ;m5:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC=1C=CC(=C(C#N)C1)ON=C(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In 400 ml of DMF was dissolved acetone oxime (34.5 g) followed by potassium t-butoxide (51 g). After this mixture had stirred for 30 minutes, 5-methoxy-2-nitro-benzonitrile (70 g) was added. After stirring overnight, the reaction was diluted with ether (~4 L) and filtered. The filtrate was washed with ethyl acetate and combined organics were washed with water (3×1.5 L), dried (MgSO4) and concentrated in vacuo. Preparative liquid chromatography (silica gel) eluting with 4:1 heptane/EtOAc yielded the expected product (10 g). |
Here is a chemical reaction formula: Reactants are m4_m1:COC=1C=CC(=C(C#N)C1)ON=C(C)C, amount is: 0.0 ;m3:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 MOLE;m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m1:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=NOC2=C1C=C(C=C2)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In 125 ml of dry methanol was dissolved 5-methoxy-2-[[(1-methylethylidene)amino]oxy]benzonitrile (10 g), followed by 125 ml of ethereal hydrochloric acid. The reaction was stirred under nitrogen overnight. The reaction was neutralized with saturated sodium carbonate solution and extracted with EtOAc. The organic layer was dried and concentrated in vacuo. Recrystallization of the residue from dichloromethane/petroleum ether afforded the expected product (6.8 g). |
Here is a chemical reaction formula: Reactants are m4:CC(=O)C.C(Cl)(Cl)(Cl)Cl, amount is: 0.0 MOLE;m5_m8:BrBr, amount is: 0.0 ;m1_m6_m2_m7_m3:ClC1=NOC2=C1C=CC(=C2)OC, amount is: 0.0 ;m1_m6_m2_m7_m3:BrBr, amount is: 0.0 ;m1_m6_m2_m7_m3:N#N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5_m8:C(C)(=O)O, amount is: 0.0 ;m1_m6_m2_m7_m3:C(C)(=O)O, amount is: 0.0 ;m1_m6_m2_m7_m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC1=C(C=CC=2C(=NOC21)Cl)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3-chloro-6-methoxy-1,2-benzisoxazole (25 g) in acetic acid (200 ml) was added a solution of bromine (32.6 g) in acetic acid (100 ml) dropwise under N2 at ambient temperature. The mixture was allowed to stir overnight. TLC (silica gel, 5% acetone/CCl4) revealed the presence of starting material. Additional bromine (11 g) in acetic acid (50 ml) was added, and the reaction mixture was allowed to stir overnight. The reaction was filtered and washed with water. The precipitate was collected and recrystallized from methanol to yield the desired compound, m.p. 134°-135° C. |
Here is a chemical reaction formula: Reactants are m1_m6_m2_m7:NC1=NOC2=C1C=CC(=C2)OC, amount is: 0.0 ;m1_m6_m2_m7:BrBr, amount is: 0.0 ;m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 MOLE;m3:BrBr, amount is: 0.0 MOLE;m5:[O-]S(=O)[O-].[Na+].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m6_m2_m7:CO, amount is: 0.0 ;m1_m6_m2_m7:CO, amount is: 0.0 ;m8:CC(=O)C.C(Cl)(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:NC1=NOC2=C1C=C(C(=C2)OC)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3-amino-6-methoxy-1,2-benzisoxazole (14 g) in methanol (1 L) was added a solution of bromine (13.6 g) and methanol (200 ml) dropwise at -50° C. under N2. The mixture was allowed to warm to room temperature after the addition was complete. After 24 hours an additional 1/4 equivalent of bromine was added. TLC (10% acetone/CHCl3) showed no starting material 24 hours later. The reaction was neutralized with saturated K2CO3 solution, treated with saturated Na2SO3 solution triturated with water, filtered, and washed with water. The crude product was dried in vacuo affording 14 g of product, m.p. 226°-227° C. |
Here is a chemical reaction formula: Reactants are m1_m3:COCOC1=CC2=C(C(=NO2)NCCN2CCSCC2)C=C1, amount is: 0.0 ;m2:C(=O)([O-])[O-].[Na+].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(CCSCC1)CCNC1=NOC2=C1C=CC(=C2)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6-Methoxymethoxy-N-[2-(4-thiomorpholinyl)ethyl]-1,2-benzisoxazol-3-amine (1.6 g Example 22) was dissolved in methanolic hydrochloric acid (40 ml) and stirred under nitrogen for 24 hours. The reaction was neutralized with saturated Na2CO3 solution, and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo. The resulting residue was filtered through a silica gel filter-cake eluting with 5% MeOH/DCM, concentrated in vacuo, and subsequent titration with EtOAc provided the product (1.0 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:N1=CC=C(C=C1)N1C(CNCC1)C1=NOC2=C1C=CC(=C2)O, amount is: 0.0 ;m1_m3_m2:CN(C(=O)Cl)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C(OC1=CC2=C(C(=NO2)C2N(CCNC2)C2=CC=NC=C2)C=C1)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 3-[1-(4-pyridyl)piperazinyl]-1,2-benzisoxazol-6-ol (0.80 g) in pyridine (10 ml) was added dimethylcarbamyl chloride (0.70 g) under N2. The reaction was heated to 85° C. for 2 hours. TLC (silica gel 30% MeOH/CH2Cl2) showed no starting material was present. The solvent was removed in vacuo and the residue was flash chromatographed (silica gel) eluting with 7% MeOH/CH2Cl2 to afford 0.80 g of material. The material was further purified through recrystallization from CH2Cl2 /pet. ether to afford 0.70 g of the product, m.p. 171°-172° C. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC1=NOC2=C1C=CC(=C2)OC, amount is: 0.0 ;m1_m2:N1=C(C=CC=C1)N1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC1=CC2=C(C(=NO2)C2N(CCNC2)C2=NC=CC=C2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A sealed tube was charged with 3-chloro-6-methoxy-1,2-benzisoxazole (0.25 g, 1.4mmol) and 1-(2-pyridyl)piperazine (0.67 g, 4 mmol) and heated to 140° C. overnight. The reaction was cooled to room temperature, diluted with methanol, and concentrated in vacuo. The material was flash chromatographed (silica gel) eluting with CH2Cl2. The material was further purified through recrystallization from 1,2-dichloroethane/pet. ether to afford 0.15 g of the product, m.p.=123°-124° C. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m2_m3:[Cl-].[Na+], amount is: 0.0 ;m2_m3:O, amount is: 0.0 ;m1_m5:O=C1C(CC(CC1)(C(=O)OC)C(=O)OC)C(=O)OC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1CCC(CC1)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 55 g (0.2 mole) portion of trimethyl 4-oxocyclohexane-1,1,3-tricarboxylate is dissolved in 240 ml DMF and to this is added 26 g (0.445 mole) of sodium chloride and 16 ml (0.89 mole) of water, under nitrogen. This mixture is heated to reflux and maintained for 48 hours, under nitrogen. The reaction is then stripped to dryness under reduced pressure, the residue added to water and the crude product extracted into dichloromethane (3×100 ml). The combined extracts are dried over MgSO4 and stopped to dryness, giving a yellow oil. This crude product is vacuum-distilled to obtain methyl 4-oxocyclohexane-1-carboxylate (b.p. 82°-108° C. at 1.0 mm Hg) which is used directly in the next step. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:O=C1CCC(CC1)C(=O)OC, amount is: 0.0 ;m1_m4_m2_m3:C(CO)O, amount is: 0.0 ;m1_m4_m2_m3:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O1CCOC12CCC(CC2)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 8 g (0.51 mole) of methyl 4-oxocyclohexane-1-carboxylate in 50 ml of dry benzene is added 4 g (0.064 mole) of ethylene glycol and 0.10 g of p-toluenesulfonic acid and this mixture is refluxed overnight with a Dean-Stark apparatus. The cooled reaction is allowed to stand and the bottom layer (ethylene glycol) separated and the remaining benzene layer washed with aqueous sodium bicarbonate, dried over MgSO4, and stripped to dryness, giving methyl 1,4-dioxaspiro[4,5]decane-8-carboxylate as a clear liquid residue. This material is used without further purification in the next step. |
Here is a chemical reaction formula: Reactants are m4:ClCCl, amount is: 0.0 MOLE;m3:O, amount is: 0.0 ;m1_m5:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ;m2:O1CCOC12CCC(CC2)C(=O)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NCC1CCC2(OCCO2)CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 1.4 g (0.037 mole) of lithium aluminum hydride in 100 ml dry THF is added, portionwise, 4.9 g (0.026 mole) of 1,4-dioxaspiro[4,5]decane-8-carboxamide over one-half hour. This mixture is then refluxed 2 hours, then allowed to cool to room temperature. About 5 ml water is added cautiously and then stirred 15 minutes. Dichloromethane is then added and the insolubles filtered off. The organic layer is dried over MgSO4 and stripped to dryness, giving 3.48 g crude product. This material is vacuum-distilled to obtain 8-aminomethyl-1,4-dioxaspiro[4,5]decane (b.p. 84°-101° C. at 0.7 mm Hg.) |
Here is a chemical reaction formula: Reactants are m1_m2:C=O, amount is: 0.0 ;m1_m2:OS(=O)(=O)O, amount is: 0.0 MOLE;m3_m4:NCC1CCC2(OCCO2)CC1, amount is: 0.0 ;m3_m4:CCO, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:N12CC3C(C(CC(C1)C3)C2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Paraformaldehyde (2.2 g), in 320 ml 2% v/v H2SO4, is heated to boiling and 2.7 g (0.016 mole) of 8-aminomethyl-1,4-dioxaspiro[4,5]decane in 20 ml EtOH, is added over 4 hours. This mixture is then heated at reflux for 24 hours. The cooled reaction is washed with dichloromethane, then basified with 10N NaOH and extracted with dichloromethane. The combined extracts are dried over MgSO4 and stripped to dryness, giving 1.68 g (69%) of product. |
Here is a chemical reaction formula: Reactants are m3:FC(S(=O)(=O)OC1=NC(=CC(=C1[N+](=O)[O-])NCCCC)C)(F)F, amount is: 0.0 ;m2:C(C)N(CC)CC, amount is: 0.0 ;m1:C(C1=CC=CC=C1)NCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCC)NC1=C(C(=NC(=C1)C)N(CC1=CC=CC=C1)CC1=CC=CC=C1)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dibenzylamine (1.04 g, 5.28 mmole), triethylamine (0.53 g, 5.28 mmole), 4-butylamino-6-methyl-3-nitro-2-pyridinyl trifluoromethanesulfonate (1.72 g, 5.28 mmole) and toluene (45 mL) were combined and heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature then filtered through a layer of silica gel. The silica gel was eluted with methylene chloride. The combined organic filtrates were evaporated to provide 2.08 g of an oily semisolid. |
Here is a chemical reaction formula: Reactants are m3:[BH4-].[Na+], amount is: 0.0 ;m1_m6_m4:[BH4-].[Na+], amount is: 0.0 ;m2_m5:CC1=CC(=C(C(=N1)N(CC1=CC=CC=C1)CC1=CC=CC=C1)[N+](=O)[O-])NCC(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m4:CO, amount is: 0.0 ;m2_m5:C(Cl)Cl, amount is: 0.0 ,Catalysts are m1_m6_m4:O.[Ni](Cl)Cl, amount is: 0.0 .Products are 0:CC1=CC(=C(C(=N1)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N)NCC(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium borohydride (585 mg, 16 mmole) was added to a solution of nickel (II) chloride hydrate (1.02 g, 4.3 mmole) in methanol (100 mL). The addition caused a black solid to form along with gas evolution. The resulting heterogeneous mixture was stirred at ambient temperature for 30 minutes. A solution containing 6-methyl-N4 -(2-methylpropyl)-3-nitro-N2,N2 -bis(phenylmethyl)pyridine-2,4-diamine (3.47 g, 8.6 mmole) in methylene chloride (20 mL) was added followed by the addition of sodium borohydride (1.37 g, 36 mmole). The reaction mixture was stirred at ambient temperature for about 30 minutes then eluted through a layer of silica gel with a methanol/methylene chloride mixture. The filtrate was concentrated under vacuum. The resulting residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried with magnesium sulfate and concentrated under vacuum to provide 2.74 g of the desired product as a green foam. |
Here is a chemical reaction formula: Reactants are m1_m2_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m5:CC1=CC(=C(C(=N1)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N)NCCC1=CC=CC=C1, amount is: 0.0 ;m3:C(C)(=O)Cl, amount is: 0.0 ;m4:C(C)(=O)OCC.CCCCCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m5:C(Cl)Cl, amount is: 0.0 ;m6_m7:O, amount is: 0.0 MOLE;m6_m7:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)(=O)C=1C(=C(C(=NC1C)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N)NCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Triethylamine (2 mL) was added to a solution of 6-methyl-N4 -(2-phenylethyl)-N2,N2 -bis(phenylmethyl)-pyridine-2,3,4-triamine (6 g, 14.2 mmole) in methylene chloride (50 mL). Acetyl chloride (1.1 mL, 15.5 mmole) was slowly added to the reaction mixture which was then heated on a steam bath for about 1 hour. The reaction mixture was stirred at ambient temperature overnight then diluted with water and methylene chloride. The organic phase was separated, washed with water, dried over magnesium sulfate and then concentrated under vacuum to provide a light green solid. This solid was slurried with ethyl acetate/hexane then recrystallized from ethyl acetate/hexane to provide 4.1 g of a white solid. A small portion (0.8 g) was purified by silica gel column chromatography to provide the desired compound as a white solid, m.p. 152°-153° C. Analysis: Calculated for C30H32N4O: % C, 77.56; % H, 6.94; % N, 12.06; Found: % C, 77.61; % H, 6.89: % N, 12.05. |
Here is a chemical reaction formula: Reactants are m2:P(=O)(Cl)(Cl)Cl, amount is: 0.0 MOLE;m1_m3:ClC1=C(C2=C(C(=N1)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N=C(N2C(C)(C)C)C)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C1(=CC=CC=C1)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C(C2=C(C(=N1)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N=C(N2)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The material from Example 32 was diluted with toluene then combined with phosphorous oxychloride and heated at reflux overnight. The reaction mixture was concentrated under vacuum. The residue was diluted with water, basified with ammonium hydroxide then extracted several times with methylene chloride. The methylene chloride extracts were combined, dried over magnesium sulfate then concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with 10-40% ethyl acetate in hexane to provide the desired product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:[I-].[Na+], amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m5:ClC1=C(C2=C(C(=N1)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N=C(N2)C)C, amount is: 0.0 ;m4:C(C)OCCBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C2=C(C(=N1)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N=C(N2CCOCC)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium iodide (1.5 g) and potassium carbonate (1 g) were added to a solution of 6-chloro-2,7-dimethyl-N4,N4 -bis(phenylmethyl)-1H-imidazo[4,5-c]pyridin-4-amine (1.0 g, 2.7 mmole) in acetone (250 mL). 2-Bromoethyl ethyl ether (0.5 mL, 4.4 mmole) was added and the reaction mixture was heated at reflux overnight. The reaction mixture was filtered and the filtrate concentrated under vacuum. The residue was partitioned between methylene chloride and water. The methylene chloride phase was separated, dried with magnesium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with 10-30% ethyl acetate in hexane to provide 0.7 g of the desired product. |
Here is a chemical reaction formula: Reactants are m2:C(C)(=O)Cl, amount is: 0.0 ;m3:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ;m1:C(CCC)NC1=C(C(=NC(=C1)C)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCC)N1C(=NC=2C(=NC(=CC21)C)N(CC2=CC=CC=C2)CC2=CC=CC=C2)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N4 -n-Butyl-6-methyl-N2,N2 -bis(phenylmethyl)pyridine-2,3,4-triamine (0.65 g, 1.7 mmole) was combined with toluene (10 mL) and acetyl chloride (0.12 mL, 1.7 mmole) and stirred at ambient temperature for 15 minutes. Phosphorous oxychloride (0.31 mL) was added and the reaction mixture was heated at reflux overnight. The reaction mixture was evaporated. The residue was purified by silica gel column chromatography eluting with hexane:ethyl acetate (70:30) to provide 0.18 g of the desired product. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C1(=CC=CC=C1)CC(=O)Cl, amount is: 0.0 ;m1_m2_m4:CC=1C(=C(C(=NC1C)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N)NCCC1=CC=CC=C1, amount is: 0.0 ;m3:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C2=C(C(=N1)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N=C(N2CCC2=CC=CC=C2)CC2=CC=CC=C2)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylacetyl chloride (0.6 mL, 4.5 mmole) was added to a solution of 5,6-dimethyl-N4 -(2-phenylethyl)-N2,N2 -bis(phenylmethyl)pyridine-2,3,4-triamine (1.96 g, 4.5 mmole) in methylene chloride (100 mL) and the resulting mixture was stirred at ambient temperature overnight. A catalytic amount of p-toluenesulfonic acid was added and stirring was continued at ambient temperature over the weekend. The reaction mixture was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate then concentrated under vacuum to provide an oil. The oil was purified by silica gel column chromatography eluting with 5-10% ethyl acetate in hexane to provide 1.8 g of the desired product as a white solid, m.p. 139°-141° C. Analysis: Calculated for C37H36N4 : % C, 82.80; % H, 6.76; % N, 10.44; Found: % C, 82.86; % H, 6.78; % N, 10.36. |
Here is a chemical reaction formula: Reactants are m2_m4:CC=1N(C2=C(C(=NC(=C2C)C)N(CC2=CC=CC=C2)CC2=CC=CC=C2)N1)CC(C)C, amount is: 0.0 ;m3:CI, amount is: 0.0 ;m1:C(CCC)[Li], amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m4:O1CCCC1, amount is: 0.0 ;m5_m6:O, amount is: 0.0 MOLE;m5_m6:C(C)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)C=1N(C2=C(C(=NC(=C2C)C)N(CC2=CC=CC=C2)CC2=CC=CC=C2)N1)CC(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Butyllithium (0.5 mL of 2.5M in hexanes) was added to a cooled (-78° C.) solution of 2,6,7-trimethyl-1-(2-methylpropyl)-N4,N4 -bis(phenylmethyl)-1H-imidazo[4,5-c]pyridin-4-amine (0.5 g, 1.2 mmole) in tetrahydrofuran (30 mL). The reaction mixture was allowed to warm to -10° C. then it was cooled to -78° C. and combined with methyl iodide (0.23 mL, 3.6 mmole). The reaction mixture was allowed to warm to ambient temperature then diluted with water and diethyl ether. The ether layer was separated, washed with ammonium chloride solution, dried over magnesium sulfate and then concentrated to provide 0.5 g of the desired product. |
Here is a chemical reaction formula: Reactants are m3:O, amount is: 0.0 MOLE;m2:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE;m7_m1_m4:CC=1N(C2=C(C(=NC(=C2)C)N(CC2=CC=CC=C2)CC2=CC=CC=C2)N1)CCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CO, amount is: 0.0 MOLE;m7_m1_m4:C(=O)O, amount is: 0.0 ,Catalysts are m7_m1_m4:[OH-].[OH-].[Pd+2], amount is: 0.0 .Products are 0:CC=1N(C2=C(C(=NC(=C2)C)N)N1)CCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium hydroxide on carbon (0.5 g, Pearlman's catalyst) was added to a mixture of 2,6-dimethyl-1-(2-phenylethyl)-N4,N4 -bis(phenylmethyl)-1H-imidazo[4,5-c]pyridin-4-amine (2.3 g, 5.15 mmole) in formic acid (10 mL). The reaction mixture was heated at reflux overnight. An additional 0.5 g of catalyst was added and refluxing was continued overnight. The reaction mixture was neutralized with saturated sodium bicarbonate solution, diluted with methanol then filtered through a layer of celite to remove the catalyst. The celite layer was flushed with methylene chloride and methanol. The filtrates were combined and concentrated under vacuum to provide a mixture of water and a solid. This mixture was extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate and concentrated under vacuum to provide 1.2 g of a tan solid. This solid was recrystallized from ethanol to provide 0.24 g of the desired product as a solid, m.p. 185°-187° C. Analysis: Calculated for C16H18N4 : % C, 72.15; % H, 6.81; % N, 21.04; Found: % C, 71.51; % H, 6.88; % N, 20.61. |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 ;m1:ClC1=C(C2=C(C(=N1)N(CC1=CC=CC=C1)CC1=CC=CC=C1)N=C(N2CCOCC)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:CO, amount is: 0.0 MOLE,Catalysts are m4:[OH-].[OH-].[Pd+2], amount is: 0.0 MOLE.Products are 0:C(C)OCCN1C(=NC=2C(=NC=C(C21)C)N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6-Chloro-1-(2-ethoxyethyl)-2,7-dimethyl-N4,N4 -bis(phenylmethyl)-1H-imidazo[4,5-c]pyridin-4-amine (0.7 g, 1.56 mmole) was taken up in methanol saturated with anhydrous hydrochloric acid (100 mL), combined with palladium hydroxide on carbon and then hydrogenated on a Paar apparatus for four hours. The reaction mixture was filtered to remove the catalyst then concentrated under vacuum. The residue was partitioned between methylene chloride/water/sodium bicarbonate. The methylene chloride layer was separated, dried over magnesium sulfate then concentrated under vacuum to provide an off white solid. This material was recrystallized from ethyl acetate/hexane to provide 0.18 g of the desired product as a solid, m.p. 129°-130° C. Analysis: Calculated for: C12H18N4O+1/4H2O: % C, 60.35; % H, 7.81; % N, 23.46; Found: % C, 60.64; % H, 7.50; % N, 23.39. |
Here is a chemical reaction formula: Reactants are m4:CCOCC, amount is: 0.0 MOLE;m3:Cl, amount is: 0.0 ;m2:Br, amount is: 0.0 ;m1:NC1=NC(=C(C2=C1N=C(N2CC(O)(C)C)CCCC)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:Cl.C(CCC)C=1N(C2=C(C(=NC(=C2C)C)N)N1)C=C(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Amino-2-butyl-α,α,6,7-tetramethyl-1H-imidazo[4,5-c]pyridine-1-ethanol (about 200 mg) was combined with concentrated hydrobromic acid (50 mL) and heated at reflux overnight. The reaction mixture was concentrated under vacuum. The residue was taken up in methanol then diluted with ether. The resulting precipitate was collected then partitioned between methylene chloride and 10% sodium hydroxide. The organic layer was separated, dried over magnesium sulfate then concentrated to provide an oil. The oil was taken up in methanol then combined with 0.05 mL of concentrated hydrochloric acid followed by dilution with ether. The resulting precipitate was collected, rinsed with ether and dried to provide 60 mg of the desired product as a white solid, m.p. 205° C. (dec.). Analysis: Calculated for C16H24N4 +1.6 HCl: % C, 58.10; H, 7.80; % N, 16.94; Found: % C, 57.95; % H, 7.87; % N, 16.89. |
Here is a chemical reaction formula: Reactants are m3:S, amount is: 0.0 MOLE;m1_m2_m4:C(#N)C1=CC=C(C=C1)NC(NC(=O)C1=CC=C(OCC(=O)OC)C=C1)=O, amount is: 0.0 ;m1_m2_m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(N)(=S)C1=CC=C(C=C1)NC(NC(=O)C1=CC=C(OCC(=O)OC)C=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of the product of step (a) (600 mg), pyridine (56 ml) and triethylamine (8 ml) was covered with a blanket of H2S gas and stirred at ambient temperature overnight. The dark green reaction mixture was evaporated to dryness and the residue was stirred with dry ether for 1 hour. The resultant solid was collected and washed thoroughly with ether to give methyl 4-[4-(4-thiocarbamoylphenyl)allophanoyl]phenoxyacetate (593 mg) as a yellow solid; m.p. 215°-218° C. (decomposes); NHR Spectrum (DMSO-d6 +CD3CO2D) 3.73 (3H, s), 4.90 (2H, s), 7.08 (2H, d), 7.64 (2H, d), 7.98 (2H, d), 8.06 (2H, d); Mass Spectrum m/Z 388 (M+H)+. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 ;m1_m5_m7_m6:C1(=CC=CC=C1)C1CCNCC1, amount is: 0.0 ;m1_m5_m7_m6:CO, amount is: 0.0 ;m3:[C-]#N.[Na+], amount is: 0.0 ;m2:OO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m7_m6:O, amount is: 0.0 ,Catalysts are m1_m5_m7_m6:O.O.[O-][W](=O)(=O)[O-].[Na+].[Na+], amount is: 0.0 .Products are 0:C(#N)C1N(CCC(C1)C1=CC=CC=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 4-phenylpiperidine (10 g, 0.062 mole) in methanol (30 mL), was added a solution of sodium tungstate dihydrate (0.82 g, 2.48 mmole) in water (7 mL). With stirring at 0°, hydrogen peroxide (30%, 13.9 mL, 0.136 mole) was added dropwise. After complete addition, the reaction mixture was stirred for an additional 3 hours, and then sodium cyanide (4.56 g, 0.093 mole) was added, followed by 4 N HCl (22 mL, 0.088 mole). The reaction mixture was stirred overnight during which time it warmed to room temperature. The solid was collected by filtration through glass sinter funnel, and the solution was neutralized to pH 7 and was extracted with dichloromethane. The organic extract was combined with the solid and dried over MgSO4 and evaporated. Flash column purification eluting with 40% ethyl acetate in hexane gave 2-cyano-1-hydroxy-4-phenylpiperidine(8.6 g). |
Here is a chemical reaction formula: Reactants are m3:OO, amount is: 0.0 ;m1_m2_m4:C(C1=CC=CC=C1)C=1C=NC=CC1, amount is: 0.0 ;m1_m2_m4:OO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)C=1C=[N+](C=CC1)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3-benzylpyridine (25 g, 0.148 tool) in hydrogen peroxide (30%, 15.1 mL) and acetic acid (100 mL) was refluxed for one day. Then more hydrogen peroxide (3 mL) was added and the resulting mixture was refluxed overnight. The reaction mixture was then evaporated and partitioned between a mixture of 3 N HCl, brine and dichloromethane. The organic layer was separated, dried and evaporated to give the desired compound (27.6 g, 100%). |
Here is a chemical reaction formula: Reactants are m1_m2:N([C@H](CC1=C(NC2=CC=CC=C12)C#N)C(=O)N[C@H](CCCC)C(=O)OC)C(=O)OC(C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N[C@H](CC1=C(NC2=CC=CC=C12)C#N)C(=O)N[C@H](CCCC)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of Boc-DTrp(2-CN)-DNle-OMe (52 mg, prepared in Example (2-b)) in formic acid (5 mL) was stirred at room temperature for 1 h, and then evaporated. The residue was dissolved in ethyl acetate (60 mL) and the solution was washed with sat. aq. NaHCO3 (30 mL) and brine (30 mL), dried over MgSO4 and evaporated under reduced pressure to give the product (40 mg). |
Here is a chemical reaction formula: Reactants are m1_m2:N([C@H](CC1=C(NC2=CC=CC=C12)C#N)C(=O)N[C@H](CC(OC)=O)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N[C@H](CC1=C(NC2=CC=CC=C12)C#N)C(=O)N[C@H](CC(OC)=O)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of Boc-DTrp(2-CN)-DAsp(OMe)-OtBu (78 mg, prepared in Example (9-a)) in formic acid (3 mL) was stirred at room temperature for 1 h and evaporated under reduced pressure. The residue was dissolved in ethyl acetate (30 mL), and the solution was washed with sat. aq. NaHCO3 (20 mL×2), dried over MgSO4 and evaporated under reduced pressure to give the product (53 mg). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:N1([C@H](C(=O)N[C@H](C(C)(C)SC)C(=O)N[C@@H](CC(C)C)C(=O)OC)CCC1)C(=O)OC(C)(C)C, amount is: 0.0 ;m1_m3_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1([C@H](C(=O)N[C@H](C(C)(C)SC)C(=O)N[C@@H](CC(C)C)C(=O)O)CCC1)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of Boc-Pro-DPen(Me)-Leu-OMe (0.94 g, prepared in Example (9-e)) in methanol (2.5 mL) was added 1N NaOH (2.5 mL) under ice-cooling. The mixture was stirred under ice-cooling for 30 min and at room temperature for 1 h. The mixture was evaporated under reduced pressure to remove methanol and water (20 mL) was added to the residue. The mixture was extracted with diethyl ether (20 mL). The aqueous layer was acidified with 10% aq. citric acid and extracted with ethyl acetate (10 mL×3). The combined ethyl acetate extracts were washed with brine (10 mL), dried over MgSO4 and evaporated under reduced pressure to give the product (0.94 g). |
Here is a chemical reaction formula: Reactants are m3_m4:C=1C=CC2=C(C1)N=NN2O.O, amount is: 0.0 ;m3_m4:CCN=C=NCCCN(C)C.Cl, amount is: 0.0 ;m1_m2_m5:N[C@H](CC1=C(NC2=CC=CC=C12)C#N)C(=O)N[C@H](CC(OC)=O)C(=O)OC(C)(C)C, amount is: 0.0 ;m1_m2_m5:N1([C@H](C(=O)N[C@H](C(C)(C)SC)C(=O)N[C@@H](CC(C)C)C(=O)O)CCC1)C(=O)OC(C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(C)(=O)OCC, amount is: 0.0 ;m1_m2_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1([C@H](C(=O)N[C@H](C(C)(C)SC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CC2=C(NC3=CC=CC=C23)C#N)C(=O)N[C@H](CC(OC)=O)C(=O)OC(C)(C)C)CCC1)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of H-DTrp(2-CN)-DAsp(OMe)-OtBu (26 mg, prepared in Example (9-b)) and Boc-Pro-DPen(Me)-Leu-OH (33 mg, prepared in Example (9-f)) in DMF (3 mL) were added HOBT·H2O (12 mg) and EDCI·HCl (15 mg) under ice-cooling. The mixture was stirred under ice-cooling for 1 h and at room temperature for 1.5 h. The mixture was diluted with ethyl acetate (30 mL), washed with sat. aq. NaHCO3 (15 mL), 10% aq. citric acid (15 mL) and brine (15 mL) successively, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=30/1 for development to give the product (42 mg). |
Here is a chemical reaction formula: Reactants are m5_m6:Cl, amount is: 0.0 ;m5_m6:[Cl-].[Na+], amount is: 0.0 MOLE;m1_m7_m2:ClS(=O)(=O)N=C=O, amount is: 0.0 ;m1_m7_m2:C(C1=CC=CC=C1)O, amount is: 0.0 ;m3_m8_m4:Cl.COC(C(CCC)N)=O, amount is: 0.0 ;m3_m8_m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m7_m2:C(Cl)Cl, amount is: 0.0 ;m3_m8_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C(CCC)NS(=O)(=O)NC(=O)OCC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 7.36 ml (84.9 mmol) of chlorosulfonyl isocyanate in 150 ml of methylene chloride was added benzyl alcohol (8.82 ml, 84.7 mmol) at 0°-5° C. After stirring the above solution for 1.5 hours at this temperature, a solution of 15.62 g (93.25 mmol) of 2-amino-pentanoic acid methyl ester hydrochloride in 500 ml of methylene chloride containing triethylamine (25.54 g, 0.2528 mol) was added at 0°-5° C., and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride/ethyl acetate (4:1, 2×200 ml) and the combined organic layer was washed with brine, dried and concentrated in vacuo to yield 28.2 g (87.6%) of 2-(N-carbobenzyloxyaminosulfonyl) aminopentanoic acid methyl ester (Formula XIV: R=CH3, R1 =H; R2 =propyl; R3 =H) as a solid, m.p. 76°-78° C. |
Here is a chemical reaction formula: Reactants are m1_m2:COC(C(CCC)NS(=O)(=O)NC(=O)OCC1=CC=CC=C1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:CO, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:COC(C(CCC)NS(=O)(=O)N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2- (N-carbobenzyloxyaminosulfonyl) aminopentanoic acid methyl ester (26.7 g) in methanol (200 ml) under nitrogen was cooled to 0° C. and 1.5 g of 10% Pd/C was added. The mixture was placed into a Parr Apparatus and hydrogenated for 2 hours. The catalyst was removed on a pad of CELITE® and the filtrate was concentrated in vacuo and purified by flash silica gel chromatography (4-6% methanol in methylene chloride) to afford 11.0 g (62%) of 2-(aminosulfonylamino)pentanoic acid methyl ester (Formula VII: R=CH3 ; R1 =H; R2 =propyl; R3 =H) as a solid, m.p. 63°-64° C. |
Here is a chemical reaction formula: Reactants are m2:C1(=CC=CC=C1)SCCl, amount is: 0.0 ;m1:C(CC)C1C(NS(N1)(=O)=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C1(=CC=CC=C1)C, amount is: 0.0 ,Catalysts are m4:[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:C1(=CC=CC=C1)SCN1S(NC(C1=O)CCC)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1dioxide (1.0 g, 5.6 mmol) suspended in 15 ml of toluene containing tetrabutylammonium bromide (0.18 g, 0.56 mmol) was added phenylthiomethyl chloride (0.98 g, 6.2 mmol) and the resulting mixture was refluxed (120° C.) for 20 hours. The mixture was cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel flash column chromatography (20% of ethyl acetate in hexane) to afford 1.16 g of 2-phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =propyl; R3 =H). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(=CC=CC=C1)SCN1S(NC(C1=O)CCC)(=O)=O, amount is: 0.0 ;m1_m3_m2:S(=O)(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCN1S(NC(C1=O)CCC)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-phenylthiomethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1.1 g, 3.6 mmol) in 10 ml of methylene chloride was added sulfuryl chloride (0.44 ml, 5.5 mmol) and the mixture was stirred for 3 hours at room temperature. The mixture was concentrated in vacuo, the residue triturated in hexane (50ml) for 1 hour, the resulting solid filtered and purified by silica gel flash column chromatography (20-25% of ethyl acetate in hexane) to afford 0.31 g of 2-chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula II: R1 =H; R2 =propyl; R3 =H; X'=Cl) as a solid, m.p. 62°-63.5° C. |
Here is a chemical reaction formula: Reactants are m3_m7_m8:Cl.COC(C(N)C(C)C)=O, amount is: 0.0 ;m3_m7_m8:C(Cl)Cl, amount is: 0.0 MOLE;m1_m6_m2:ClS(=O)(=O)N=C=O, amount is: 0.0 ;m1_m6_m2:C(C1=CC=CC=C1)O, amount is: 0.0 ;m1_m6_m2:C(Cl)Cl, amount is: 0.0 ;m4_m5:Cl, amount is: 0.0 ;m4_m5:[Cl-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m7_m8:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C(CCC)NS(=O)(=O)NC(=O)OCC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 7.36 ml (84.9 mmol) of chlorosulfonyl isocyanate in 150 ml of methylene chloride was added benzyl alcohol (8.82 ml, 84.7 mmol) at 0° C. over a period of 35 minutes. After stirring the above solution for 2 hours at this temperature, a solution of 15.62 g (93.25 mmol) of DL-valine methyl ester hydrochloride in methylene chloride containing triethylamine (36 67 ml) was added at 0°-5° C. and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride (2×200 ml) and the combined organic layer was washed with brine, dried, and concentrated in vacuo to yield 30 g of N-(carbobenzyloxyaminosulfonyl)-DL-valine methyl ester (Formula XIV: R=CH3 ; R1 =H; R2 =isopropyl; R3 =H) as a solid. |
Here is a chemical reaction formula: Reactants are m1_m2:COC(C(NS(=O)(=O)NC(=O)OCC1=CC=CC=C1)C(C)C)=O, amount is: 0.0 ;m1_m2:CO, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:COC(C(CCC)NS(=O)(=O)N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of N- (carbobenzyloxyaminosulfonyl) -DL-valine methyl ester (28.5 g) in methanol (200 ml) under nitrogen was cooled to 0° C. and 1.8 g of 10% Pd/C was added. The mixture was placed into a Parr Apparatus and hydrogenated at 55 psi for 2 hours. The catalyst was removed on a pad of CELITE® and the filtrate was concentrated in vacuo and purified by flash silica gel chromatography (ethyl acetate/hexane, 1:1) to afford 17.2 g (96%) of N-(aminosulfonyl)-DL-valine methyl ester (Formula VII: R=CH3 ; R1 =H; R2 =isopropyl; R3 =H) as a solid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:C[O-].[Na+], amount is: 0.0 ;m1_m3_m2_m4:COC(C(NS(=O)(=O)N)C(C)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:CO, amount is: 0.0 ;m1_m3_m2_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CC)C1C(NS(N1)(=O)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of freshly prepared sodium methoxide (6.41 g, from 2.3 g of Na) in 100 ml of methanol was added to a solution of N-(aminosulfonyl)-DL-valine methyl ester (10.5 g; 0.05 mmol) in methanol (150 ml) and the resulting reaction mixture was stirred at room temperature for 6 hours. The mixture was cooled, neutralized with BIO-RAD® 50W-X8 H+ ion exchange resin, and filtered. The filtrate was concentrated in vacuo to yield a solid residue which was crystallized from methanol/hexane to afford 16.4 g of a crude 4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =H; R2 =isopropyl; R3 =H). |
Here is a chemical reaction formula: Reactants are m3:C1(=CC=CC=C1)C, amount is: 0.0 ;m2_m4:C1(=CC=CC=C1)SCCl, amount is: 0.0 ;m1:C(C)(C)C1C(NS(N1)(=O)=O)=O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m2_m4:[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:C1(=CC=CC=C1)SCN1S(NC(C1=O)CCC)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 4-isopropyl-1,2, 5-thiadiazolidin-3-one 1, 1-dioxide (7.0 g, 39.32 retool) suspended in 150 ml of toluene was added phenylthiomethyl chloride (6.83 g, 43 mmol) and tetrabutylammonium bromide (1.26 g, 3.93 retool). The resulting mixture was refluxed for 17 hours, cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford 5.2 g of 2-phenylthiomethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =isopropyl; R3 =H) . |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:COC(C(CCC)NS(=O)(=O)N)=O, amount is: 0.0 ;m1_m3_m2_m4:C[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:CO, amount is: 0.0 ;m1_m3_m2_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CC)C1C(NS(N1)(=O)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2- (aminosulfonyl) aminopentanoic acid methyl ester (13 g; 0.05 retool) in methanol (150 ml) was added to a solution of sodium methoxide (5.54 g, from 2 g of Na) in 150 ml of methanol and the resulting reaction mixture was refluxed for 18 hours. The mixture was cooled, neutralized with BIO-RAD® 50W-X8 H+ ion exchange resin, and filtered. The filtrate was concentrated in vacuo to yield an oil which was crystallized from methanol/hexane to afford 10.8 g (quantitative) of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =H; R2 =propyl; R3 =H). |
Here is a chemical reaction formula: Reactants are m3:CI, amount is: 0.0 ;m1_m2_m4:CC(C)([O-])C.[K+], amount is: 0.0 ;m1_m2_m4:C1(=CC=CC=C1)CN1S(NC(C1=O)CCC)(=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)CN1S(N(C(C1=O)CCC)C)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Potassium t-butoxide (1.05 g, 9.37 mmol) was added to a solution of 2-phenylmethyl-4-propyl-1,2, 5-thiadiazolidin-3-one 1,1-dioxide (2.4 g, 8.95 mmol) in 25 ml of THF at 0° C. and the mixture was stirred at this temperature for 1 hour. To the mixture was added methyl iodide (6.35 g, 44.73 mmol) and the resulting mixture was allowed to stir at 0° C. for 0.5 hour and at room temperature for 4 hours. The resulting mixture was quenched with saturated ammonium chloride, extracted with ethyl acetate and the organic layer was washed with brine. The organic layer was dried, concentrated in vacuo, and the residue was purified by flash chromatography to afford 2.4 g (95%) of 2-phenylmethyl-4-propyl-5-methyl-1,2,5-thiadiazol-idin-3-one 1,1-dioxide (Formula XI: R1 =H; R2 =propyl; R3 =CH3) as an oil. |
Here is a chemical reaction formula: Reactants are m1:C(=O)[O-].[NH4+], amount is: 0.0 ;m2_m4:C1(=CC=CC=C1)CN1S(N(C(C1=O)CCC)C)(=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m3:CO, amount is: 0.0 ;m2_m4:CO, amount is: 0.0 ,Catalysts are m5_m3:[Pd], amount is: 0.0 .Products are 0:C(CC)C1C(NS(N1C)(=O)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 3.5 g of 10% Pd/C in 150 ml of methanol containing ammonium formate (14 g) was added a solution of 2-phenylmethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (8.7 g) in 40 ml of methanol under nitrogen. The mixture was stirred at room temperature for 15 hours, filtered through a pad of CELITE® and the residue was washed with methanol. The combined filtrate was concentrated in vacuo to afford 7.6 g of 4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =H; R2 =propyl; R3 =CH3) as a solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(CC)C1C(NS(N1C)(=O)=O)=O, amount is: 0.0 ;m1_m2_m3:C1(=CC=CC=C1)SCCl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1(=CC=CC=C1)C, amount is: 0.0 ,Catalysts are m1_m2_m3:[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:C1(=CC=CC=C1)SCN1S(N(C(C1=O)CCC)C)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-propyl-5-methyl-1, 2,5-thiadiazolidin-3-one 1,1-dioxide (9 g) , phenylthiomethyl chloride (7.43 g) and tetrabutylammonium bromide (1 g) was suspended in 200 ml of toluene, refluxed for 8 hours, cooled, and concentrated in vacuo. The residue was purified by flash chromatography (15-20% ethyl acetate in hexane) to afford 8.5 g (88%) of 2-phenylthiomethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =propyl; R3 =CH3) as an oil. |