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Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:C1(=CC=CC=C1)CC=O, amount is: 0.0 ;m1_m3_m2_m4:C(=C)[Mg]Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:O1CCCC1, amount is: 0.0 ;m1_m3_m2_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=C)C(CC1=CC=CC=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of phenylacetaldehyde(600 mg, 5 mmol) in 12 ml of tetrahydrofuran was added dropwise over about 10 minutes to a solution of vinyl magnesium bromide (10 ml; 1M in tetrahydrofuran; 10 mmol) in 12 ml of tetrahydrofuran at 0° C. The internal temperature was maintained below 5° C. during the addition. After stirring for 1 hour at 0° C., the reaction was quenched by adding about 25 ml of saturated ammonium chloride solution. The resulting mixture was extracted with 100 ml of ethyl ether. The organic layer was washed with saturated ammonium chloride solution(50 ml) and brine(50 ml). Drying over magnesium sulfate and concentrating afforded 750 mg of the title product as a light orange liquid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:CC(C)(C)C1(OC1)CO, amount is: 0.0 ;m1_m3_m2_m4:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:C(C)OCC, amount is: 0.0 ;m1_m3_m2_m4:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C[C@](CO)(C(C)(C)C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-(1,1-dimethylethyl)-2-oxiranemethanol (2.3 g, 17.7 mmol) in ethyl ether (10 ml) was added to a suspension of lithium aluminum hydride (1.477 g, 38.9 mmol) in ethyl ether (100 ml) at -5° C. and stirred at room temperature for 30 minutes. The mixture was cooled to 0° C., quenched with 10% aqueous sulfuric acid saturated with sodium sulfate. The aqueous layer was extracted with ethyl acetate and the combined extracts were washed with saturated sodium bicarbonate and brine and dried (magnesium sulfate). Concentration in vacuo followed by recrystallization from hexane gave 1.5 g of (R)-2,3,3-trimethyl-1,2-butanediol as a white solid. |
Here is a chemical reaction formula: Reactants are m4:C(C)N(CC)CC, amount is: 0.0 ;m1_m5_m2:CS(=O)C, amount is: 36.29999923706055 MILLIMOLE;m1_m5_m2:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m3_m6:C[C@](CO)(C(C)(C)C)O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m7:C(Cl)Cl, amount is: 0.0 MOLE;m1_m5_m2: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:C[C@](C=O)(C(C)(C)C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of dimethylsulfoxide (2,578 ml. 36.3 mmol) in methylene chloride (3 ml) was added dropwise at -78° C. to a stirred solution of oxalyl chloride (1.585 ml, 18.2 mmol) over 5 minutes and stirred at -78° C. for 10 minutes. A solution of (R)-2,3,3-trimethyl-1,2-butanediol in methylene chloride (25 ml) was added dropwise and stirred for 15 minutes at -78° C. Triethylamine (11.51 ml, 82.6 mmol) was added and the reaction was allowed to come to room temperature. The mixture was diluted with additional methylene chloride, washed with 10% sulfuric acid, the combined aqueous phase was extracted with methylene chloride, and the combined organic layer was washed with saturated sodium bicarbonate, dried (magnesium sulfate), and concentrated by distillation at atmospheric pressure to afford 2.15 g of (R)-2,3,3-trimethyl-2-hydroxybutanal as a pale gummy solid. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m1_m2_m3_m5:Cl(=O)[O-].[Na+], amount is: 0.0 ;m1_m2_m3_m5:S(N)(O)(=O)=O, amount is: 0.0 ;m1_m2_m3_m5:C[C@](C=O)(C(C)(C)C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6_m7:C(Cl)Cl, amount is: 0.0 MOLE;m6_m7:CSC, amount is: 0.0 ;m1_m2_m3_m5:O1CCCC1.O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C[C@](C(=O)O)(C(C)(C)C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium chlorite (1.81 g, 20 mmol) and sulfamic acid (1.94 g, 20 mmol) were added in succession to a stirred solution of (R)-2,3,3-trimethyl-2-hydroxybutanal (2.0 g, 15.4 mmol) in 30 ml of tetrahydrofuran-water (1:1) at 0° C. The mixture was allowed to warm to room temperature, stirred for 30 minutes, diluted with methylene chloride and about 1 ml of methyl sulfide was added followed by a small quantity of water. The organic layer was separated, the aqueous layer was extracted with methylene chloride, and the combined organic layer was dried (magnesium sulfate) and concentrated to afford a yellow gummy solid. Recrystallization from hexanes afford 1.45 g of (R) -2,3,3-trimethyl-2-hydroxybutanoic acid as a pale solid. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)NCCNCC1=CC=CC=C1, amount is: 0.0 ;m4:Br.C(C)N(CC)CC, amount is: 0.0 MOLE;m1_m5:BrC(C(=O)OCC)CBr, amount is: 0.0 ;m3:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C1=CC=CC=C1, amount is: 0.0 ;m6:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1C(CN(CC1)CC1=CC=CC=C1)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 80 g (0.31 mol) of ethyl 2,3-dibromopropionate diluted in 300 ml of benzene are added dropwise, but fairly rapidly, to a warm solution of 72 g (0.3 mol) of N,N'-dibenzylethylenediamine, 700 ml of benzene and 50 ml (0.36 mol) of triethylamine. After the addition, reflux is maintained for 3 hours (triethylamine hydrobromide precipitates in the reaction mixture). The mixture is cooled and filtered through fritted glass, and the solid is washed with ether. The flitrate is washed with 200 ml of saturated sodium hydrogen carbonate solution and then twice with 100 ml of water. The organic phases are dried over magnesium sulfate and the solvents are evaporated off in vacuo. Approximately 100 ml of toluene are added, and evaporation is continued. The resulting residue is diluted in 400 ml of absolute ethanol and saturated with gaseous hydrogen chloride. The salt precipitates by the addition of ether. Filtering, washing with ether and drying yield from 100 to 110 g of white crystals. |
Here is a chemical reaction formula: Reactants are m1:C(C1=CC=CC=C1)NC(C)O, amount is: 0.0 ;m2:C(=O)O, amount is: 0.0 ;m3:C=O, amount is: 0.0 MOLE,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)N(C)C(C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture consisting of 151 g (1 mol) of N-benzylaminoethanol, 120 ml of 90% formic acid, 120 ml of a 35% aqueous formaldehyde solution and 1 liter of methanol is heated under reflux for 20 hours. The solvent is evaporated off in vacuo and the residue is treated with an aqueous sodium hydroxide solution and then extracted with methylene chloride. After customary treatment, the product is purified by distillation. 138 g of the desired product are obtained. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)N, amount is: 0.0 ;m1_m3:C(C1=CC=CC=C1)N(CCCl)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ;m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N(CCNCC1=CC=CC=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 128 g (0.7 mol) of the compound obtained in Step b dissolved in 600 ml of ethanol are added dropwise to 150 g ( 1.4 mol) of benzylamine diluted in 200 ml of warm ethanol. The mixture is stirred at room temperature for 24 hours and the solvent is evaporated off in vacuo. Benzylamine hydrochloride crystallises from a mixture of methylene chloride and acetone, and is removed by filtration. The tiltrates are saturated with gaseous hydrogen chloride and the hydrochloride of the desired compound crystallises from a methylene chloride/ether mixture. 105 g of white crystals are obtained. |
Here is a chemical reaction formula: Reactants are m3_m6:ClC1=C(CN2C(C(N(CC2)C)=O)(C(=O)OCC)C)C=CC(=C1)Cl, amount is: 0.0 ;m1:B(F)(F)F, amount is: 0.0 MOLE;m4:Cl, amount is: 0.0 MOLE;m5:[OH-].[Na+], amount is: 0.0 MOLE;m2:[BH4-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m6:O1CCCC1, amount is: 0.0 ;m7:O1CCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C(CN2C(CN(CC2)C)(C(=O)OCC)C)C=CC(=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4.4 ml of freshly distilled boron trifluoride are added dropwise, while cold, to 1.1 g of dry sodium borohydride suspended in 35 ml of freshly distilled tetrahydrofuran. The reaction mixture is stirred at 0° C. for 2 hours and then 3.5 g (0.01 mol) of the compound obtained in Step g in 100 ml of tetrahydrofuran are added. The mixture is then heated under reflux for one hour and then 50 ml of a 2N hydrochloric acid solution are added while cold. The mixture is neutralised with sodium hydroxide and then extracted with ether. Customary treatment of the organic phase yields a crude product which is purified over a silica gel column (eluant: trichloromethane). 1 g of the pure desired product is obtained in the form of a colourless oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=C(CN2C(CNCC2)C(=O)OCC)C=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:CO, amount is: 0.0 ;m1_m2_m3_m4:C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(CN2C(CN(CC2)C)C(=O)OCC)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 28 g (0.1 mol) of the compound obtained in Step b, 120 ml of methanol, 12 ml of 37% formaldehyde and 12 ml of formic acid is heated under reflux for 20 hours. The solvent is evaporated off in vacuo and the resulting residue is taken up in ether and a saturated sodium hydrogen carbonate solution. The organic phase is washed, neutralised and then extracted with ether. After drying over magnesium sulfate and evaporation of the solvent, the residue is dissolved in 200 ml of absolute ethanol and saturated with gaseous hydrochloric acid. The dihydrochloride precipitates by the addition of ether. 32 g of white crystals are isolated. |
Here is a chemical reaction formula: Reactants are m3:[C-]#N.[K+], amount is: 0.0 MOLE;m4_m5:C(C1=CC=CC=C1)N1C(CN(CC1)CC1=CC=CC=C1)CCl, amount is: 0.0 ;m1_m2:[C-]#N.[K+], amount is: 0.0 ;m1_m2:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1C(CN(CC1)CC1=CC=CC=C1)CC#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4.57 g (70.2 mmol) of potassium cyanide and 10 ml of water is heated to reflux. When the potassium cyanide has dissolved, 17 g (54 mmol) of the chloride obtained in Step b dissolved in 10 ml of ethanol are added slowly. When the addition is complete, the mixture is heated under reflux for 3 hours. After evaporation of the solvent, the mixture is taken up in chloroform and washed with water until the pH is neutral. The chloroform phase is dried over magnesium sulfate, filtered and evaporated off. The resulting residue is crystallised from hexane and yields 13.2 g of white crystals. |
Here is a chemical reaction formula: Reactants are m1:C(C)OC(=O)C1NCCNC1, amount is: 0.0 MOLE;m2:C(C)(C)Br, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)(C)N1C(CN(CC1)C(C)C)C=1NCCN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Reacting 2-ethoxycarbonylpiperazine with 2,2 aquivalents of isopropyl bromide in the same conditions as for example 21, and treating the obtained product in the same conditions as for example 1, step d, the desired product is obtained. |
Here is a chemical reaction formula: Reactants are m2:CC1CCNCC1, amount is: 0.0 ;m1_m3:C(=C)C1=NC(=NO1)C1=CN(C2=CC=CC=C12)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1CCN(CC1)CCC1=NC(=NO1)C1=CN(C2=CC=CC=C12)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Ethenyl-3-(1-methyl-1-H-indol-3-yl)-1,2,4-oxadiazole (D2)(0.0254 g, 1.13 mmol) was dissolved in methanol (5 ml) and 4-methyl piperidine (0.167 ml, 1.69 mmol) was added. The mixture was left standing at room temperature for 16 hours, before being evaporated under reduced pressure to give a colourless oil, which was purified by silica-gel chromatography, eluting with ethyl acetate to afford the title compound as a colourless oil that crystallised on standing. The material was then converted to its hydrochloride salt, mp 192°-192° C. |
Here is a chemical reaction formula: Reactants are m1:ClC(C1=NC(=NO1)C1=CN(C2=CC=CC=C12)C)(Cl)Cl, amount is: 0.0 ;m2:NCCN1CCCCC1, 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(CN1CCCCC1)C1=NC(=NO1)C1=CN(C2=CC=CC=C12)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Trichloromethyl-3-[1-methyl-1H-indol-3-yl]-1,2,4-oxadiazole (0.100 g, 0.316 mmol) (D8) was dissolved with stirring in 1-(2-aminoethyl) piperidine (0.8 ml) and heated to 120° C. After 0.5 h, the reaction mixture was allowed to cool and was partitioned between EtOAc and water. The organic layer was then washed with water (1×), dried (Na2SO4) and evaporated under reduced pressure to give a yellow oil which was purified by silica gel chromatography (10% MeOH in EtOAc as eluant) to give the title compound as a colourless oil that crystallised on standing (0.095 g, 93%). |
Here is a chemical reaction formula: Reactants are m1_m5:C(#N)C1=CN(C2=CC=CC=C12)C, amount is: 0.0 ;m4:[OH-].[Na+], amount is: 0.0 MOLE;m2_m3:[Cl-].[NH4+], amount is: 0.0 ;m2_m3:[N-]=[N+]=[N-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m1_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN1C=C(C2=CC=CC=C12)C1=NN=NN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-Cyano(1-methyl-1H-indole) (J. Med. Chem. 199, 34, 147) (0.500 g, 3.21 mmol) was dissolved in dry DMF (4 ml) and treated with ammonium chloride (0.214 g, 4.01 mmol) and sodium azide (0.260 g, 4.01 mmol). The mixture was then heated to reflux with stirring. After 26 h, the reaction mixture was allowed to cool and was evaporated under reduced pressure to give a brown oil. Water (15 ml) was added to this residue whereupon it solidified. The mixture was made strongly basic with sodium hydroxide solution and then extracted with diethyl ether. The aqueous layer was then treated with activated charcoal and heated on a water bath for 10 minutes. The mixture was then filtered and the filtrate acidified with 5M HCl to pH4. The resulting brown precipitate was then filtered off and dried in vacuo to give the title compound (0.125 g, 20%) as a pale brown solid. |
Here is a chemical reaction formula: Reactants are m1_m5:CN1C=C(C2=CC=CC=C12)C1=NN=NN1, amount is: 0.0 ;m4_m7:BrCC(=O)N1CCCCC1, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m3_m6:BrCC(=O)N1CCCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C1CCOC1, amount is: 0.0 ;m4_m7:C1CCOC1, amount is: 0.0 ;m3_m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)N1C(CCCC1)N1N=NC(=N1)C1=CN(C2=CC=CC=C12)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-(1-Methyl-1H-indol-3-yl)tetrazole (0.080 g, 0.402 mmol) was dissolved in dry THF (5 ml) and treated with sodium hydride (80%) (0.014 g, 0.441 mmol). When effervescence had ceased, 1-(bromoacetyl)piperidine (Bull. Soc. Chim. France 1964 5, 1063) (0.093 g, 0.422 mmol) in dry THF (2 ml) was added. After 1 h, a further amound of 1-(bromoacetyl)piperidine (0.047 g, 0.211 mmol) in dry THF (1 ml) was added. After a further 2 h, the reaction mixture was evaporated under reduced pressure to give a brown solid which was partitioned between CHCl3 and water. The organic layer was washed with NaHCO3 solution, and the combined aqueous layers were extracted with CHCl3. The combined organic layers were then dried (Na2SO4) and evaporated to give an off white foam which was dried in vacuo and then purified by silica-gel chromatography (pentane: EtOAc 1:1 as eluant) to give the title compound (D3 ) as a white solid (0.080 g, 61%) |
Here is a chemical reaction formula: Reactants are m3:BrCC(=O)N1CCCCC1, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m1:CN1C=C(C2=CC=CC=C12)C1=NNC=N1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1CCOC1, amount is: 0.0 ;m5:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)N1C(CCCC1)N1N=C(N=C1)C1=CN(C2=CC=CC=C12)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-(1-Methyl-1H-indol-3-yl)-1,2,4-triazole (0.190 g, 0.960 mmol) was dissolved with stirring in dry THF (5 ml) and was treated with sodium hydride (80%) (0.032 g, 1.05 mmol), followed by 1-(bromoacetyl)piperidine (Bull. Soc, Chim. Fr. 1964, 5, 1063-9) (0.232 g, 1.05 mmol) in dry THF (1 ml). After 4 h, the reaction mixture was evaporated under reduced pressure and partitioned between EtOAc and water. The organic layer was then dried (Na2SO4) and evaporated under reduced pressure to give a yellow oil, which was purified by silica-gel chromatography (EtOAc→EtOAc:MeOH 100:1 as eluant) to give the title compound (D5b) as a white solid (0.080 g, 26%). |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:NC=1C=NC=CC1, amount is: 0.0 ;m1_m2_m4_m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m4_m3:ClC(=O)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OCC1=CC=CC=C1)NC=1C=NC=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-aminopyridine (10 g, 0.106 mol) and triethyl amine (16.3 mL, 0.117 mol) in dichloromethane (100 mL) at 0° C., was added benzyl chloroformate (15.2 mL, 0.106 mol) slowly. The reaction mixture was stirred overnight and was washed with water, saturated NaHCO3, dried over MgSO4, and evaporated. The residue was purified on a silica gel column to give the product (9.51 g) |
Here is a chemical reaction formula: Reactants are m2:BrCCCCCC#N, amount is: 0.0 ;m1:C1(=CC=CC=C1)C1=CC(NC(=C1)C1=CC=CC=C1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1(=CC=CC=C1)C, amount is: 0.0 ,Catalysts are m3:C([O-])([O-])=O.[Ag+2], amount is: 0.0 .Products are 0:C1(=CC=CC=C1)C1=CC(=NC(=C1)C1=CC=CC=C1)OCCCCCC#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The procedure of Example 4 is followed using 4,6-diphenyl-2-pyridone (6.18 g) and 6-bromohexanonitrile (6.60 g) in place of 6-bromohexanoate, silver carbonate (6.89 g) and toluene (300 cc) and the reaction mixture is refluxed for 72 hours. The material formed is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 9.5-0.5) to obtain 6-[(4,6-diphenyl-2-pyridyl)oxy]hexanonitrile as a white solid which is used directly in subsequent reactions. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C1(=CC=CC=C1)C1=CC(=CC(=N1)OCCCCCC#N)C1=CC2=C(C=C1)OCO2, amount is: 0.0 ;m1_m2_m3_m4:[N-]=[N+]=[N-].[Na+], amount is: 0.0 ;m1_m2_m3_m4:Cl.C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CN1C(CCC1)=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C1=CC(=CC(=N1)OCCCCCC1=NN=NN1)C1=CC2=C(C=C1)OCO2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: By using a similar procedure to that described in example 9 but with 2.4 g 6-{[6-phenyl-4-(3,4-methylenedioxyphenyl)-2-pyridyl]oxy}hexanonitrile, 1.65 g of sodium azide, 1.3 g of triethylamine hydrochloride (in place of ammonium chloride) and 90 cc of N-methylpyrrolidone (in place of dimethylformamide) as the starting material (70 hours; 150° C.), and after purification by flash chromatography on silica gel (30-60mm; eluent: ethyl acetate) and recristallization from 18 cc of acetonitrile gives 5-{5-{[6-phenyl-4-(3,4-methylenedioxyphenyl)-2-pyridyl]oxy}pentyl }-1H-tetrazole (m.p.=150° C.) |
Here is a chemical reaction formula: Reactants are m3:C(C)O, amount is: 0.0 ;m2:[OH-].[K+], amount is: 0.0 MOLE;m1:NC1=CC=C(C=C1)C1=CC(=NC(=C1)C1=CC=CC=C1)OCCCCCC(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=CC=C(C=C1)C1=CC(=NC(=C1)C1=CC=CC=C1)OCCCCCC(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The procedure in Example 4 is followed but using ethyl 6-{[4-(4-aminophenyl)-6-phenyl-2-pyridyl]-oxy}hexanoate (3.9 g), potassium hydroxide pellets (0.81 g) dissolved in distilled water (10 cc), and ethanol (150 cc). The reaction mixture is refluxed for 2 hours. The product is purified by recrystallization in toluene (70 cc) to obtain 6-{[4-(4-aminophenyl)-6-phenyl-2-pyridyl]oxy}hexanoic acid as yellowish crystals; (m.p.=131°-133° C.) |
Here is a chemical reaction formula: Reactants are m2:N1CCCC1, amount is: 0.0 ;m1_m3:C1(=CC=CC=C1)C1=CC(=NC2=CC=CC=C12)OCCCCCC(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C1=CC(=NC2=CC=CC=C12)OCCCCCC(=O)N1CCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 5 g of 6-[(4-phenyl-2-quinolyl)oxy]hexanoic acid in 120 cc of tetrahydrofuran is added 2.9 g of 1,1'-carbonyldiimldazole. The mixture is stirred for 2 hours to 50 C. After cooling, 1.3 g of pyrrolidine is added and the mixture is stirred at room temperature overnight. The tetrahydrofuran is removed in vacuo and the residue partitioned between ethyl acetate and water. The ethyl acetate solution is washed with water, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue is then purified by flash chromatography on silica gel (30-60mm; eluent: 3:7 cyclohexane/ethyl acetate) to give 1-[6-(4-phenyl-2-quinolyloxy)hexanoyl]pyrrolidine as a white solid (m.p.=52°-54° C.) |
Here is a chemical reaction formula: Reactants are m2:NCCCCC(C(=O)OC)(C)C, amount is: 0.0 ;m1:ClC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1, 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:CC(C(=O)OC)(CCCCNC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3.2 g of 2-chloro-4-phenyl-quinoline (prepared according to the method of S. Kwon and K. Isagawa, Yoki Gosei Kagaku Shi 1973,31, 313) and 5.9 g of methyl 6-amino-2,2-dimethylhexanoate is heated to 100 C. for 8 hours. After cooling, the residue is purified by chromatography on silica gel (eluent: 98:2 dichloromethane/methanol). to give methyl 2,2-dimethyl-6-[(4-phenyl-2-quinolyl)amino]hexanoate obtained as an oil. |
Here is a chemical reaction formula: Reactants are m1_m5_m2:CC(C(=O)OC)(CCCCS)C, amount is: 0.0 ;m1_m5_m2:[H-].[Na+], amount is: 0.0 ;m3_m6:ClC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1, amount is: 0.0 ;m4:CO, 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:CC(C(=O)OC)(CCCCSC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4 g of methyl 2,2-dimethyl-6-mercaptohexanoate in 100 cc of dimethylformamide, is added 0.55 g of sodium hydride (50% w/w dispersion in mineral oil). The mixture is stirred for 2 hours until effervescence has stopped. A solution of 5 g of 2-chloro-4-phenylquinoline in 50 cc of dimethyl-formamide is then added. The obtained mixture is heated to 60 C. for 8 hours. After cooling, 10 cc of methanol is added and the mixture evaporated. The resultant residue is purified by flash chromatography on silica gel (30-60 mm; eluent: 8:2 hexane/ethyl acetate) to give methyl 2,2-dimethyl-6-[(4-phenyl-2-quinolyl)thio]-hexanoate is obtained as an oil. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:C(C)(=O)NC1=C(C(=O)C=2SC=CC2)C=CC=C1, amount is: 0.0 ;m1_m4_m2:CC[O-].[Na+], amount is: 0.0 ;m3:CC[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C(C)O, amount is: 0.0 ;m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:S1C(=CC=C1)C1=CC(NC2=CC=CC=C12)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-(2-acetylaminobenzoyl)thiophene (4.8 g) in ethanol (60 cc) is added sodium ethylate (3.2 g). The reaction mixture is refluxed for 9 hours, treated again with sodium ethylate (0.5 g) and then allowed to reflux for 10 hours. The mixture is poured in iced water (200 cc). The precipitate formed is filtered, washed with distilled water until neutrality and then with acetone (3×50 cc) and dried at 40° C. under reduced pressure. The residue thus obtained is recrystallized in ethanol to obtain the product as a yellow solid. (m.p.=262°-264° C.) |
Here is a chemical reaction formula: Reactants are m1_m2:C1(=CC=CC=C1)C=1C=C(C=C(C1)C1=CC=CC=C1)OC, amount is: 0.0 ;m1_m2:Cl.[NH+]1=CC=CC=C1, 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:C1(=CC=CC=C1)C=1C=C(C=C(C1)C1=CC=CC=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4.7 g of 3,5-diphenyl-anisole and 5.3 g of pyridinium hydrochloride was heated for 5 hours to 185° C. After cooling, the residue was partitioned between 100 cc of diethyl ether and 120 cc of water. The organic layer wes then washed with water, dried (Na2SO4) and evaporated. The resultant residue was suspended in 50 cc of n-hexane and filtered to give 3.75 g (85%) of 3,5-diphenyl-phenol as a white solid. (m.p.=97° C.) |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C1(=CC=CC=C1)C=1C=C(OCCCCCC(=O)OCC)C=C(C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:[OH-].[K+], amount is: 0.0 ;m1_m2_m3_m4:O, amount is: 0.0 ,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:C1(=CC=CC=C1)C=1C=C(OCCCCCC(=O)O)C=C(C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: By using a similar procedure to that described in example 1 but with 1 g of ethyl 6-(3,5-diphenyl-phenoxy)hexanoate, 0.22 g of potassium hydroxide in pellets, 5 cc of water and 5 cc of ethanol as the starting material (2 hours; reflux), and after recrystallization in a mixture of 10 cc of n-hexane and 2 cc of ethyl acetate, 0.5 g (54%) of 6-(3,5-diphenyl-phenoxy)hexanoic acid was obtained as a white solid. (m.p.=104° C.) |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C1=CC=CC=C1)C=1C=C(C=O)C=CC1, amount is: 0.0 ;m1_m2_m3_m4:[I-].C(=O)(O)CCCCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:CC(C)(C)[O-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)C=1C=C(C=CC1)C=CCCCCC(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: By using a similar procedure to that described in example 24 but with 1 g of 3-benzylbenzaldehyde, 5.5 g of (6-carboxyhexyl)triphenylphosphonium iodide, 2.5 g of potassium ter-butylate and 40 cc of toluene as the starting material (1 hour; 50° C.), and after purification by flash chromatography on silica gel (30-60 Mm; eluent: 8:2:0.05 n-hexane/ethyl acetate/acetic acid), 7-(3-benzyl-phenyl)-6-heptenoic acid is obtained. (m.p.=68° C.) |
Here is a chemical reaction formula: Reactants are m3:CN(C=O)C, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE;m1_m2_m5:C(CCC)[Li], amount is: 0.0 ;m1_m2_m5:ClC1=C(C(=C(S1)Cl)Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7_m6:CCCCCC, amount is: 0.0 MOLE;m7_m6:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m2_m5:O1CCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C(SC(=C1Cl)Cl)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Butyllithium (2.5 molar in tetrahydrofuran, 3.96 mL, 9.9 mmol) is added to a solution of tetrachlorothiophene (2.00 g, 9.01 mmol) in tetrahydrofuran at 0° C. The reaction mixture is stirred at 0° C. for 30 minutes, warmed to room temperature over 45 minutes, treated with N,N-dimethylformamide (0.79 g, 10.8 mmol), stirred for three hours, poured into one molar hydrochloric acid at 4° C. and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to obtain a brown solid. Flash chromatography of the solid using silica gel and a 5% ethyl acetate in hexane solution gives a beige solid which is recrystallized from ethyl acetate and hexane to obtain the title product as beige needles (1.63 g, 84%, mp 81°-82° C.). |
Here is a chemical reaction formula: Reactants are m4_m7:BrCC(=O)C(F)(F)F, amount is: 0.0 ;m3_m6:ClC1=C(SC(=C1Cl)Cl)C#N, amount is: 0.0 ;m1_m2_m5:C(C)#N, amount is: 0.0 ;m1_m2_m5:C(C)(C)[N-]C(C)C.[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m7:C(C)(=O)O, amount is: 0.0 MOLE;m8:O, amount is: 0.0 MOLE;m3_m6:O1CCCC1, amount is: 0.0 MOLE;m10_m9_m0:CCCCCC, amount is: 0.0 MOLE;m10_m9_m0:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m2_m5:O1CCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C(SC(=C1Cl)Cl)C=1NC(=CC1C#N)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Acetonitrile (0.97 g, 23.7 mmol) is added dropwise to a solution of lithium diisopropylamide (two molar in hydrocarbons, 10.9 mL, 21.8 mmol) in tetrahydrofuran at -78° C. The reaction mixture is stirred at -78° C. for 30 minutes, treated with a solution of 3,4,5-trichloro-2-thiophenecarbonitrile (3.87 g, 18.2 mmol) in tetrahydrofuran, stirred for 30 minutes at -78° C., warmed to room temperature over 45 minutes, quenched with saturated ammonium chloride solution and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to obtain a red solid. A mixture of the red solid and 1-bromo-3,3,3-trifluoroacetone (1.95 mL, 18.7 mmol) in acetic acid is refluxed for three hours and 30 minutes, diluted with water and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated .in vacuo to obtain a red solid. Flash chromatography of the solid using silica gel and a 15% ethyl acetate in hexane solution gives the title product as a white solid (0.49 g, 7.8%, mp 220°-221° C.). |
Here is a chemical reaction formula: Reactants are m4_m7_m0:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m2_m3_m5:C(C)OCCl, amount is: 0.0 ;m1_m2_m3_m5:BrC=1C(=C(NC1C(F)(F)F)C=1SC(=C(C1Cl)Cl)Cl)C#N, amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m7_m0:CCCCCC, amount is: 0.0 MOLE;m1_m2_m3_m5:CN(C=O)C, amount is: 0.0 MOLE;m6:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrC=1C(=C(N(C1C(F)(F)F)COCC)C=1SC(=C(C1Cl)Cl)Cl)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Chloromethyl ethyl ether (0.20 g, 2.13 mmol) is added to a mixture of 4-bromo-2-(3,4,5-trichloro-2-thienyl)-5-(trifluoromethyl) pyrrole-3-carbonitrile (0.30 g, 0.71 mmol) and potassium carbonate (0.29 g, 2.13 mmol) in N,N-dimethylformamide. The reation mixture is stirred at room temperature for 30 minutes, diluted with water and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to obtain a clear oil. Flash chromatography of the oil using silica gel and a 15% ethyl acetate in hexane solution gives the title product as white crystals (0.24 g, 71%, mp 85°-87° C.). |
Here is a chemical reaction formula: Reactants are m4:S([O-])(O)=O.[Na+], amount is: 0.0 MOLE;m1_m2_m3_m5:BrBr, amount is: 0.0 ;m1_m2_m3_m5:O1C(=CC=C1)C=1NC(=CC1C#N)C(F)(F)F, amount is: 0.0 ;m1_m2_m3_m5:C(C)(=O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)(=O)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrC1=CC=C(O1)C=1NC(=CC1C#N)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Bromine (0.71 g, 4.42 mmol) is added to a solution of 2-(2-furyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (1.00 g, 4.42 mmol) and sodium acetate (0.36 g, 4.42 mmol) in acetic acid. The reation mixture is stirred for 15 minutes and poured into a 1% sodium bisulfite solution. The solids are filtered from the aqueous mixture, dried overnight under high vacuum and recrystallized from ethyl acetate and hexane to obtain the title product as red crystals (1.21 g, 90%, mp 224°-226° C. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 MOLE;m1_m2_m5:C(CCC)[Li], amount is: 0.0 ;m1_m2_m5:BrC1=CC=C(O1)C=1NC(=CC1C#N)C(F)(F)F, amount is: 0.0 ;m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCCCCC, amount is: 0.0 MOLE;m7:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m2_m5:O1CCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(=O)C1=CC=C(O1)C=1NC(=CC1C#N)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Butyllithium (3.45 mL, 7.78 mmol) is added dropwise to a solution of 2-(5-bromo-2-furyl)-5-(trifluoromethyl) pyrrole-3-carbonitrile (1.13 g, 3.70 mmol) in tetrahydrofuran at -78° C. The reation mixture is stirred at -78° C. for 30 minutes, warmed to room temperature, treated with N,N-dimethylformamide (1.35 g, 18.5 mmol), poured into one molar hydrochloric acid and extracted with ether and ethyl acetate. The combined organic extracts are washed sequentially with water and brine, dried over Na2SO4 and concentrated in vacuo to obtain an orange solid. Flash chromatography of the solid using silica gel and 20% to 50% ethyl acetate in hexane solutions give an orange solid which is recrystallized from ethyl acetate to obtain the title product as orange crystals (0.66 g, 70%, mp 224°-225° C.). |
Here is a chemical reaction formula: Reactants are m7:Cl, amount is: 0.0 MOLE;m6:CN(C=O)C, amount is: 0.0 ;m4_m5:CN(CCN(C)C)C, amount is: 0.0 ;m4_m5:C(CCC)[Li], amount is: 0.0 ;m3_m9:S1C=CC2=C1C=CC=C2, amount is: 0.0 ;m1_m2_m8:C(CCC)[Li], amount is: 0.0 ;m1_m2_m8:CN(CCN(C)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m9:O1CCCC1, amount is: 0.0 MOLE;m11_m10_m0:CCCCCC, amount is: 0.0 MOLE;m11_m10_m0:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m2_m8:O1CCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:S1C2=C(C=C1C=O)C=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Butyllithium (54 mL, 134 mmol) is added dropwise to a solution of N,N,N',N'-tetramethylethylenediamine (15.57 g, 134 mmol) in tetrahydrofuran under nitrogen at 0° C. The reaction mixture is treated dropwise with a solution of benzothiophene (15.00 g, 112 mmol) in tetrahydrofuran, warmed to room temperature, treated with additional N,N,N',N'-tetramethylethylenediamine (15.57 g, 134 mmol) and butyllithium (54 mL, 134 mmol), stirred at room temperature for 13 hours, cooled to 0° C., treated with N,N-dimethylformamide (24.40 g, 336 mmol), warmed to room temperature, stirred for five hours, poured into one molar hydrochloric acid and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over Na2SO4 and concentrated in vacuo to obtain an orange oil. Flash chromatography of the oil using silica gel and a 15% ethyl acetate in hexane 25 solution gives the title product as an orange oil (12.51 g, 69%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC(C(=O)OC(C(F)(F)F)=O)(F)F, amount is: 0.0 ;m1_m2_m3_m4:N1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:ClC=1C2=C(SC1C(=O)N)C=CC=C2, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE;m1_m2_m3_m4:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C2=C(SC1C#N)C=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Trifluoroacetic anhydride (11.90 g, 56.6 mmol) is added dropwise to a mixture of pyridine (5.23 g, 66.1 mmol) and 3-chlorobenzo[b]thiophene-2-carboxamide (10.0 g, 47.2 mmol) in methylene chloride at 0° C. The reaction mixture is warmed to room temperature over one hour, diluted with water and extracted with ether. The combined organic extracts are washed sequentially with water, one molar hydrochloric acid and brine, dried over MgSO4 and concentrated in vacuo to obtain a yellow solid. The solid is recrystallized from ethyl acetate and hexane to give the title product as off-white needles (8.80 g, 96%). |
Here is a chemical reaction formula: Reactants are m3:CCOCC.CCCCCC, amount is: 0.0 MOLE;m1_m4_m2_m5:BrBr, amount is: 0.0 ;m1_m4_m2_m5:C(C)(=O)C=1SC(=CC1)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 MOLE;m1_m4_m2_m5:C(Cl)(Cl)Cl, amount is: 0.0 MOLE;m1_m4_m2_m5:C(Cl)(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrCC(=O)C=1SC(=CC1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of bromine (18.90 g, 118 mmol) in chloroform is added to a solution of 2-acetyl-5-chlorothiophene (19.00 g, 118 mmol) in chloroform at 40°-45° C. The reaction mixture is stirred at room temperature for two hours and diluted with water. The organic layer is separated, dried over MgSO4 and concentrated in vacuo to give a solid. The solid is slurried in an ether/hexane solution, filtered and dried to give the title product as a solid (12.20 g, mp 68°-70° C.). |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3_m5:BrCC(=O)C=1SC(=CC1)Cl, amount is: 0.0 ;m1_m4_m2_m3_m5:C(CC#N)#N, amount is: 0.0 ;m1_m4_m2_m3_m5:CC(C)([O-])C.[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3_m5:O1CCCC1, amount is: 0.0 MOLE;m1_m4_m2_m3_m5:O1CCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(S1)C(=O)CC(C#N)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-bromo-1-(5-chloro-2-thienyl)ethanone (11.50 g, 48 mmol) in tetrahydrofuran is added to a solution of malononitrile (3.17 g, 48 mmol) and potassium tert-butoxide (5.70 g, 51 mmol) in tetrahydrofuran at 0° C. The reaction mixture is stirred for several minutes, concentrated in vacuo, diluted with water and filtered to collect solids. Flash chromatography of the solids using silica gel and a (4:1) hexane/ethyl acetate solution gives the title compound as a yellow solid, mp 155°-158° C. |
Here is a chemical reaction formula: Reactants are m3_m0:CCCCCC.C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m4_m2_m5:BrBr, amount is: 0.0 ;m1_m4_m2_m5:ClC=1NC(=CC1C#N)C=1SC(=CC1)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m5:O1CCOCC1, amount is: 0.0 MOLE;m1_m4_m2_m5:O1CCOCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrC=1C(=C(NC1C=1SC(=CC1)Cl)Cl)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of bromine (0.70 g, 4.3 mmol) in p-dioxane is added dropwise to a solution of 2-chloro-5-(5-chloro-2-thienyl)pyrrole-3-carbonitrile (1.0 g, 4.1 mmol) in p-dioxane. The reaction mixture is stirred overnight at room temperature and concentrated in vacuo to obtain a residue. Flash chromatography of the residue using silica gel and a (6:1) hexane/ethyl acetate solution gives the title product as a yellow solid, mp >200° C. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m3:[N+](=O)(O)[O-], amount is: 0.0 ;m1_m2_m5:[N+](=O)(O)[O-], amount is: 0.0 ;m1_m2_m5:ClC1=CC=C(C=C1)C1=CC(=C(N1)C(F)(F)F)C=1SC(=CC1)[N+](=O)[O-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:C(C)(=O)OC(C)=O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1NC(=C(C1[N+](=O)[O-])C=1SC(=CC1)[N+](=O)[O-])C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 90% nitric acid solution (0.02 g, 0.28 mmol) is added to a solution of 5-(p-chlorophenyl)-3-(5-nitro-2-thienyl)-2-(trifluoromethyl)pyrrole (0.13 g, 0.34 mmol) in acetic anhydride. The reaction mixture is stirred at room temperature for ten minutes, treated with additional 90% nitric acid solution (0.02 g, 0.28 mmol), stirred at room temperature for 15 minutes, poured into water, stirred at room temperature overnight and extracted with ether. The combined organic extracts are dried over MgSO4 and concentrated in vacuo to obtain the title product as a tan solid which is identified by 1HNMR spectral analysis. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m4_m2_m3_m5:ClC1=CC=C(C=C1)C1=NC(OC1=O)C(F)(F)F, amount is: 0.0 ;m1_m4_m2_m3_m5:BrC=1SC=C(C1)C=C[N+](=O)[O-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6_m7:Cl, amount is: 0.0 MOLE;m6_m7:CCOCC, amount is: 0.0 MOLE;m1_m4_m2_m3_m5:C1(=CC=CC=C1)C, amount is: 0.0 MOLE;m1_m4_m2_m3_m5:C1(=CC=CC=C1)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrC1=CC(=CS1)C(C[N+](=O)[O-])C1(OC(C(=N1)C1=CC=C(C=C1)Cl)=O)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of triethylamine (0.30 g, 3 mmol) in toluene is added to a solution of 4-(p-chlorophenyl)-2-(trifluoromethyl)-3-oxazolin-5-one (10.00 g, 38 mmol) and 2-bromo-4-(2-nitrovinyl)thiophene (8.98 g, 32 mmol) in toluene at 0° C. The reaction mixture is warmed to room temperature and diluted with dilute hydrochloric acid and ether. The organic layer is separated, dried over MgSO4, concentrated in vacuo, diluted with hexane, stirred at reflux, cooled to room temperature and decanted to obtain a clear solution. The solution is concentrated in vacuo and chromatographed to give the title product. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m4_m2_m5:BrC1=CC(=CS1)C(C[N+](=O)[O-])C1(OC(C(=N1)C1=CC=C(C=C1)Cl)=O)C(F)(F)F, amount is: 0.0 ;m3:CCCCCC.C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m7:ClCCCl, amount is: 0.0 MOLE;m6:Cl, amount is: 0.0 MOLE;m1_m4_m2_m5:C(C)#N, amount is: 0.0 MOLE;m1_m4_m2_m5:C(C)#N, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrC1=CC(=CS1)C1=C(NC(=C1)C1=CC=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of triethylamine (3.24 g, 32.1 mmol) in acetonitrile is added slowly to a solution of 2-[1-(5-bromo-3-thienyl)-2-nitroethyl]-4-(p-chlorophenyl)-2-(trifluoromethyl)-3-oxazolin-5-one (13.30 g, 26.8 mmol) in acetonitrile. The reaction mixture is stirred at room temperature for several minutes and diluted with dilute hydrochloric acid. The organic layer is separated, dried over MgSO4 and concentrated in vacuo to obtain a black residue. Column chromatography of the residue using silica gel and a (9:1) hexane/ethyl acetate solution gives several solids. One of the solids is stirred in cold 1,2-dichloroethane, filtered and dried to give 3-(5-bromo-3-thienyl)-5-(p-chlorophenyl)-2-(trifluoromethyl) pyrrole as a light tan solid, mp 112°-115° C. Another solid is diluted with hexane and the mixture is refluxed, cooled to room temperature and filtered to obtain 3-(5-bromo-3-thienyl)-5-(p-chlorophenyl)-4-nitro-2-(trifluoromethyl)pyrrole as a yellow solid, mp 174°-176° C. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m1_m2_m3_m5:BrC1=CC(=CS1)C1=C(NC(=C1[N+](=O)[O-])C1=CC=C(C=C1)Cl)C(F)(F)F, amount is: 0.0 ;m1_m2_m3_m5:BrBr, amount is: 0.0 ;m1_m2_m3_m5:C(C)(=O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C=C1)C=1NC(=C(C1[N+](=O)[O-])C1=CSC(=C1Br)Br)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3-(5-bromo-3-thienyl)-5-(p-chlorophenyl)-4-nitro-2-(trifluoromethyl)pyrrole (0.50 g, 1.1 mmol), bromine (0.20 g, 1.3 mmol) and sodium acetate (0.11 g, 1.3 mmol) in acetic acid (10 mL) is heated overnight at 50° C. and poured into water. The solids are collected and recrystallized from 1,2-dichloroethane to give the title product as a yellow solid, mp 241°-242° C. |
Here is a chemical reaction formula: Reactants are m5_m6_m3_m4_m1:C(CCCCCC#CCCCC)O, amount is: 0.0 ;m2:C(C)O[SiH](OCC)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m6_m3_m4_m1:C1CCOC1, amount is: 0.0 ;m5_m6_m3_m4_m1:O, amount is: 0.0 ,Catalysts are m5_m6_m3_m4_m1:O.O.O.[Rh](Cl)(Cl)Cl, amount is: 0.0 ;m5_m6_m3_m4_m1:O.[N+](=O)([O-])[O-].[Cu+2].O.O.O.O.[N+](=O)([O-])[O-].[Cu+2].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-], amount is: 0.0 .Products are 0:C(CCCCC\C=C/CCCC)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of rhodium(III) chloride trihydrate (1.3 mg, 0.005 mmol), copper(II) nitrate hemipentahydrate (5.8 mg, 0.025 mmol) in THF (2.5 mL) and water (0.5 mL) was added 7-dodecyn-1-ol (91 mg, 0.50 mmol). The solution was stirred for 5 minutes and then triethoxysilane (0.21 g, 0.23 mL, 1.25 mmol) was added. The solution was stirred at room temperature for 8 hours. The volatiles were removed in vacuo and a solution of hexane (5 mL) and ether (1 mL) was added. The solution was dried over magnesium sulfate and filtered through a one inch plug of silica gel. The substrate was diluted with hexane/ether (5:1). The solvent was removed in vacuo. The product was then added to a solution of 3N hydrochloric acid (3 mL) and stirred at room temperature for 1 hour. The aqueous layer was extracted with ether (3×10 mL). The combined organics were dried over magnesium sulfate and filtered. The solvent was removed in vacuo to afford 0.088 g (0.48 mmol, 96%) of Z-7-Dodecen-1-ol which was a 14:1 Z:E mixture by spectroscopic analysis. Spectral analysis of the Z-isomer: IR (neat) 3434.8, 2929.0, 2857.1, 1459.2, 1056.1 cm-1 ; 1H NMR (300 MHz, CDCl3) δ 5.33 (m, 2 H), 3.62 (t, J=6.6 Hz, 2 H), 2.01 (br d, 4 H), 1.66 - 1.5 (m, 2H), 1.33 - 1.22 (m, 11 H), 0.88 (t, J=7 Hz, 3 H); 13C NMR (75 MHz, CDCl3) δ 129.99, 129.67, 62.96, 32.74, 32.49, 31.93, 31.21, 29.69, 29.05, 28.58, 27.10, 26.90, 25.63, 22.32, 18.41, 13.99. |
Here is a chemical reaction formula: Reactants are m2_m5_m6_m3_m4_m7:C(C#CCCCCCCCCCC)O, amount is: 0.0 ;m2_m5_m6_m3_m4_m7:C(C)O[SiH](OCC)OCC, amount is: 0.0 ;m2_m5_m6_m3_m4_m7:C1CCOC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5_m6_m3_m4_m7:O, amount is: 0.0 ,Catalysts are m2_m5_m6_m3_m4_m7:O.O.O.[Rh](Cl)(Cl)Cl, amount is: 0.0 ;m2_m5_m6_m3_m4_m7:O.[N+](=O)([O-])[O-].[Cu+2].O.O.O.O.[N+](=O)([O-])[O-].[Cu+2].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-], amount is: 0.0 .Products are 0:C(\C=C/CCCCCCCCCC)O;0:C(C=CCCCCCCCCCC)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Z-2-Tridecen-1-ol was prepared according to the method of Example 6 using 2-tridecyn-1-ol (98 mg, 0.5 mmol), rhodium(III) chloride trihydrate (1.3 mg, 0.005 mmol), copper(II) nitrate hemipentahydrate (5.8 mg, 0.025 mmol), triethoxysilane (0.21 g, 0.23 mL, 1.25 mmol), THF (2.5 mL) and water (0.5 mL) at room temperature for 8 hours to afford 96 mg (0.48 mmol, 97%) of 2-tridecene-1-ol which was a 6:1 Z:E mixture by spectroscopic analysis. Spectral analysis of the Z-isomer: IR (neat) 3337.2, 2924.8, 2854.6, 1462.6, 1016.2 cm-1 : 1H NMR (300 MHz, CDCl3) δ 5.56 (m, 2 H), 4.17 (d, J=5.9 Hz, 2H), 2.04 (br p, 2 H), 1.24 (m, 17 H), 0.86 (t, J=6.7 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 1133.22, 58.58, 31.91, 29.62, 29.49, 29.34, 29.23, 27.44, 22.69, 15.24, 14.11. |
Here is a chemical reaction formula: Reactants are m2:[SiH2](O[*:2])[*:1], amount is: 0.0 MOLE;m1_m3:CC=1C(C(=O)O)C=CCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C1CCCC2CCCCC12, amount is: 0.0 ;m4:CCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 2-methyl-l,4-dihydrobenzoic acid (0.085 g, 0.50 mmol; 81% pure, from Aldrich Chemical Company) in decalin (5 mL) under a nitrogen atmosphere was added the polysiloxane matrix material containing a homogeneous dispersion of metal particles (0.100 g as prepared according to Example 1). The solution was heated to reflux for 19 hours. On cooling the reaction mixture was diluted with hexane (25 mL) and extracted with aqueous sodium hydroxide (5%) solution (2×5 mL). The basic aqueous solution was acidified and extracted with chloroform (3×4 mL). The combined organic layer was dried over anhydrous sodium sulfate. Removal of solvent on rotary evaporator gave 2-methylbenzoic acid (0.065 g. 96%). IR(KBr) 3600-2000 (br), 2923, 1694, 1300, 920,731 cm-1. 1H NMR (300 MHz, CDCl3) δ 8.03 (ddd, J=8.5, 3.0, 1.5 Hz, 1 H), 7.42 (td, J=8.5, 1.5 Hz, 1H), 7.26 (td, J=8.5, 1.5 Hz, 1 H), 7.22 (dd, J=8.5, 1.5 Hz, 1 H), 2.64 (s, 3H). |
Here is a chemical reaction formula: Reactants are m2:[SiH2](O[*:2])[*:1], amount is: 0.0 MOLE;m1_m4:CC=1C(C(=O)O)C=CCC1, amount is: 0.0 ;m6_m3:[Al], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1CCCC2CCCCC12, amount is: 0.0 ;m5:CCCCCC, amount is: 0.0 ,Catalysts are m6_m3:[Rh], amount is: 0.0 MOLE.Products are 0:CC1=C(C(=O)O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 2-methyl-1,4-dihydrobenzoic acid (0.085g, 0.50 mmol; 81% pure, from Aldrich Chemical Company) in decalin (5 mL) under a nitrogen atmosphere is added a polysiloxane matrix material containing a homogenous dispersion of rhodium and aluminum (0.100 g). The solution is heated to reflux for 19 hours. On cooling the reaction mixture is diluted with hexane (25 mL) and extracted with aqueous sodium hydroxide (5%) solution (2×5 mL). The basic aqueous solution is acidified and extracted with chloroform (3×4 mL). The combined organic layer is dried over anhydrous sodium sulfate. The solvent is evaporated using a rotary evaporator to give 2-methylbenzoic acid. |
Here is a chemical reaction formula: Reactants are m5_m6_m1_m3_m4:O.O.O.O.O.O.O.O.O.[N+](=O)([O-])[O-].[Al+3].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-], amount is: 0.0 ;m2:CCCCC#CCCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m6_m1_m3_m4:C1CCOC1, amount is: 0.0 ;m5_m6_m1_m3_m4:O, amount is: 0.0 ,Catalysts are m5_m6_m1_m3_m4:O.O.O.[Rh](Cl)(Cl)Cl, amount is: 0.0 ;m5_m6_m1_m3_m4:O.[N+](=O)([O-])[O-].[Cu+2].O.O.O.O.[N+](=O)([O-])[O-].[Cu+2].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-], amount is: 0.0 .Products are 0:CCCC\C=C/CCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of rhodium(III) chloride trihydrate (1.3 mg, 0.005 mmol), copper(II) nitrate hemipentahydrate (2.90 mg, 0.0125 mmol) and aluminum(III) nitrate nonahydrate (0.188 g, 0.50 mmol) in a mixture of THF (2.5 mL) and water (0.5 mL) is added 5-decyne (69 mg, 0.50 mmol). The solution is stirred for 10 minutes and then triethoxysilone (0.21 g, 1.25 mmol) is added. The system is closed and stirred at room temperature for 7 hours. The volatiles are removed in vacuo. A mixture of hexane (5 mL) and ether (1 mL) is added. The solution is dried over magnesium sulfate and filtered through a one inch plug of silica gel. The substrate is eluted with hexane/ether (5:1). The solvent is removed in vacuo to give Z-5-decene. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC=1C=C2C(=C(N(C2=CC1)C)CC(=O)O)C1=C(C=CC=C1)OC, amount is: 0.0 MOLE;m1_m2:C(C)OC1=C(N)C(=CC=C1)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC=1C=C2C(=C(N(C2=CC1)C)CC(=O)NC1=C(C=CC=C1OCC)OCC)C1=C(C=CC=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Chloro-3-(2-methoxyphenyl)-1-methylindole-2-acetic acid was reacted with 2,6-diethoxyaniline by a method similar to Example 6 to give the title compound as colorless crystals. |
Here is a chemical reaction formula: Reactants are m2_m3:BrC1=C(C=CC(=C1)Cl)OCOCCOC, amount is: 0.0 MOLE;m2_m3:FC(C1=C(C=O)C=CC=C1)(F)F, amount is: 0.0 MOLE;m1:ClC1=CC(=C(C=C1)O)C(C1=C(C=CC=C1)C(F)(F)F)=O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC=1C=CC2=C(C(=C(O2)C(=O)O)C2=C(C=CC=C2)C(F)(F)F)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 4-chloro-2-(2-trifluoromethylbenzoyl)phenol [prepared from 2-bromo-4-chloro-(2methoxyethoxy)methoxybenzene and ortho(trifluoromethyl)benzaldehyde as the starting materials: m.p. 71°-72° C. (recrystallized from hexaneisopropyl ether)] in place of 4-chloro-2-benzoylphenol in Reference Example 1, substantially the same reactions as in Step 1 to Step 3 of Reference Example 1 were conducted to give the title compound. The compounds obtained in the respective steps and their physicochemical data are shown below. |
Here is a chemical reaction formula: Reactants are m1:N1=C(N)N=C(N)N=C1N, amount is: 0.0 ;m2:N1C(=O)NC(=O)NC1=O, 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:C1(=NC(=NC(=N1)N)N)N.C1(=O)NC(=O)NC(=O)N1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Placed in a 50 ml stainless steel autoclave which was designed to permit heating up to 500° C. were 6.3 g of industrial melamine (product of Mitsui Toatsu Chemicals Inc., average particle size: 20 μm) and 6.5 g of cyanuric acid ("ICA-P", trade name; product of Shikoku Kasei Corp.; average particle size: 3.1 μm) which had been comminuted beforehand by the jet mill. The contents were gradually heated to 350 ° C. under mixing. The contents were then maintained at 350° C. under mixing for further 1 hour, whereby 12.2 g of melamine cyanurate were obtained. The yield, purity and average particle size were 98.3%, 99.6% and 18.4 μm. |
Here is a chemical reaction formula: Reactants are m2_m3:N1C(=O)NC(=O)NC1=O, amount is: 0.0 MOLE;m2_m3:N1=C(N)N=C(N)N=C1N, amount is: 0.0 ;m1:NC(=O)N, 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:C1(=NC(=NC(=N1)N)N)N.C1(=O)NC(=O)NC(=O)N1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The procedures of Example 4 were repeated except that 9 g of prilled urea (product of Mitsui Toatsu Chemicals, Inc.; melting point: 132° C.; average particle size: 1 mm) were reacted, in place of the cyanuric acid, with 4.5 g of the melamine at 300° C. As a result, melamine cyanurate was obtained in the form of a block. The yield and purity were 93% and 87.2%, respectively. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:BrN1C(CCC1=O)=O, amount is: 0.0 ;m1_m2_m3_m4:O([Si](C)(C)C(C)(C)C)C=1C=C(C(=O)N)C=CC1C, amount is: 0.0 MOLE;m1_m2_m3_m4:O([Si](C)(C)C(C)(C)C)C=1C=C(C(=O)N)C=CC1C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O([Si](C)(C)C(C)(C)C)C=1C=C(C(=O)N)C=CC1CBr, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-Bromosuccinimide (NBS) (0.507 g, 2.85 mmol) was added to a solution of 3-t-butyldimethylsiloxy-4-methyl benzamide (Compound 7.1) in 30 mL CCl4. The mixture was irradiated with a 275 W sunlamp (Sears, #34-7105) at 60° C. Each irradiation took 10 minutes followed by 10 minutes to let the lamp cool down. It took 2 hours of irradiation over a period of 4 hours to complete the reaction. After the solvent was removed at reduced pressure, the residue was subjected to flash silica gel chromatography to yield the product as a white solid (0146 g, y=81.7%). 1H NMR (CDCl3) δ 0.318 (s,6H), 1.05 (s,9H), 4.51 (s,2H), 6.10 (b, 2H), 7.25 (d,J=7.8 Hz, 1H), 7.32 (s,1H), 7.39 (d,J=7.9 Hz, 1H); --C NMR (CDCl3 ) δ 4.08, 18.28, 25.76, 27.87, 117.99, 118.07, 119.49, 131.23, 132.54, 134.97, 168.46. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(=O)OC(C)=O, amount is: 0.0 ;m1_m2_m3:FC(C=1C=CC(=NC1)CC(=O)C1=CC=C(C=C1)Cl)(F)F, amount is: 0.0 ;m1_m2_m3:CN(C)CN(C)C, 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:FC(C=1C=CC(=NC1)C(C(=O)C1=CC=C(C=C1)Cl)=C)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Acetic anhydride (19 mL, 21 g, 200 mmol) was added slowly to a stirring slurry of 2-(5-trifluoromethyl-2-pyridinyl)-1-(4-chlorophenyl)ethanone (12.1 g, 40.0 mmol) in bisdimethylaminomethane (22 mL, 16 g, 160 mmol) at 0° C. causing immediate solution. TLC showed complete conversion after 5 min and the mixture was partitioned between ether and water by adding these solvents and separating the layers. The organic layer was extracted with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure to obtain 13 g (99 percent of theory) of the title compound as a red oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC(=O)OC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:NC1=NC=C(C=C1)C(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C=1C=CC(=NC1)NC(OC1=CC=CC=C1)=O)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenyl chloroformate (1.92 g, 12.3 mmol) was added to a stirring solution of 2-amino-5-trifluoromethylpyridine (2.0 g, 12.3 mmol) in pyridine (20 mL) at a rate which maintained the temperature at 21° C. The mixture was stirred for an additional 0.5 hr and the resulting precipitate was collected by filtration, extracted with ether, then dried to obtain 2.33 g (67 percent of theory) of the title compound as white crystals melting at 203° C. |
Here is a chemical reaction formula: Reactants are m4:C(=C)C(=O)C, amount is: 0.0 ;m5:CN(C)C=O, amount is: 0.0 ;m8_m1_m7_m2:C(C)(=O)[O-].[K+], amount is: 0.0 ;m8_m1_m7_m2:C(#N)CC(=O)OCC, amount is: 0.0 ;m6:P(Cl)(Cl)Cl, amount is: 0.0 ;m3:ClC(C(=O)OCC)(Cl)C#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m8_m1_m7_m2:C(C)N(CC)CC, amount is: 0.0 ;m8_m1_m7_m2:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=NC(=CC=C1C(=O)OCC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 20 mL of toluene, 0.5 g of potassium acetate, 0.7 ml of triethylamine, and 4.25 g (40 mmol) of ethyl cyanoacetate at 5° C. were added dropwise 7.28 g (40 mmol) of ethyl 2,2-dichlorocyanoacetate. The resulting mixture was stirred at 5° C. for 30 min., and methyl vinyl ketone (4.2 g, 60 mmol) was added via a syringe pump in 1 h. After stirring at room temperature for 6 hours, 6.2 mL (80 mmol) of DMF was added, followed by slow addition of PCl3 (11 g, 80 mmol). Anhydrous HCl gas was bubbled in for 10 min., while keeping the reaction temperature around 65° C. After being heated at 80° C. for 1 hour, the reaction mixture was cooled, quenched with aqueous ammonium hydroxide, extracted with toluene, washed with 5% NaHCO3, and dried over MgSO4. Distillation afforded 5.83 g of the title compound. (36% yield, 112°-15° C./0.2 mm Hg). |
Here is a chemical reaction formula: Reactants are m4_m6:ClC(C(=O)OCC)(CCC=O)C#N, amount is: 0.0 ;m1_m5_m2:CN(C)C=O, amount is: 0.0 ;m1_m5_m2:P(Cl)(Cl)Cl, amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4_m6:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m5_m2:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=NC=CC=C1C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of DMF (5.12 g, 70 mmol) in 80 mL of toluene were added 6.85 g of PCl3 (50 mmol). Anhydrous HCl was introduced for 5 min., keeping the temperature around 60° C. Ethyl 2-chloro-2-cyano-5-oxopentanoate (10.42 g, 50 mmol) in 20 mL of toluene was added in 30 minutes. The resulting mixture was stirred for 1 h at 80° C., cooled to room temperature, quenched with water, extracted with toluene, dried over MgSO4, and concentrated and distilled to give 5.5 g of the title compound (59%). |
Here is a chemical reaction formula: Reactants are m3_m4:ClC(C(=O)OCC)(CCC=O)C#N, amount is: 0.0 ;m2:Cl, amount is: 0.0 MOLE;m5_m1:P(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4:CN(C)C=O, amount is: 0.0 ;m5_m1:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=NC=CC=C1C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 35 mL of DMF were added dropwise 6.85 g of PCl3 (50 mmol). Anhydrous HCl was introduced for 5 minutes while keeping the temperature around 70° C. Ethyl 2-chloro-2-cyano-5-oxopentanoate (7.83 g, 38.5 mmol) in 10 mL of DMF was added at 55° C. The resulting mixture was stirred for 2 h at 90° C., cooled to room temperature, quenched with water, extracted with CH2Cl2, dried over MgSO4, concentrated and distilled to give 4.4 g of the title compound (62%). |
Here is a chemical reaction formula: Reactants are m2:C(=O)C=C, amount is: 0.0 ;m1:ClC(C(=O)OCC)C#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m3:CCOC(=O)C, amount is: 0.0 ,Catalysts are m4_m3:CC(=O)[O-].[Na+], amount is: 0.0 .Products are 0:ClC(C(=O)OCC)(CCC=O)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of NaOAc (0.492 g, 6 mmol) in 200 mL of EtOAc were added at 5° C., 31.0 g (210 mmol) of ethyl chlorocyanoacetate and acrolein (14 g, 250 mmol). The resulting mixture was stirred at 35° C. for 16 hours, filtered, concentrated and distilled to give 33 g of the title compound (77%). |
Here is a chemical reaction formula: Reactants are m2:C(#N)CC(=O)OCC, amount is: 0.0 ;m3:[H][H], amount is: 0.0 MOLE;m1_m5:[H-].[Na+], amount is: 0.0 MOLE;m4:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:CS(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC(C(=O)OCC)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of NaH in 400 mL of DMSO at 20° C. were added dropwise 79.1 g of ethyl cyanoacetate (700 mmol). The solution was stirred for 1 h at 20° C. until no more hydrogen evolved from the reaction system. 156 mL (1.5 mol) of CCl4 were added carefully. Occasional cooling was applied so as to maintain the temperature between 20°-25° C. The mixture was carefully quenched with HOAc, extracted with CH2Cl2, dried over MgSO4, concentrated, and distilled to give 85.2 g of the title compound (82.5%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=NC=CC=C1C(=O)OCC, amount is: 0.0 ;m1_m2_m3:[Cl-].[NH4+], amount is: 0.0 ;m1_m2_m3:[OH-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m4:[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:ClC1=NC=CC=C1C(=O)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of ethyl 2-chloro-3-pyridinecarboxylate (1.85 g, 10 mmol), ammonium chloride (0.53 g, 10 mmol) and 15 mL of ammonium hydroxide (150 mmol) was added tetrabutylammonium bromide (0.32 g, 1 mmol). The mixture was stirred at ambient temperature for 18 hours, concentrated, washed with water and methanol, and dried to give 0.78 g (50%) of the title compound (m.p. 164°-166° C., uncorrected). |
Here is a chemical reaction formula: Reactants are m0_m2_m3_m4:ClC1=NC=CC(=C1C(=O)N)C, amount is: 0.0 ;m0_m2_m3_m4:[OH-].[Na+], amount is: 0.0 ;m0_m2_m3_m4:BrBr, amount is: 0.0 ;m1:ClC1=NC=CC=C1N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=NC=CC(=C1N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a manner similar to that described for 2-chloro-3-aminopyridine in Example 14, the title compound was prepared in 90% yield (m.p. 63°-66° C., uncorrected) from 2.57 g of 2-chloro-4-methyl-3-pyridinecarboxamide, 2.28 g of NaOH, and 3.1 g of bromine. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m6_m4_m5:ClC(C(=O)OCC)(CCC=O)C#N, amount is: 0.0 MOLE;m1_m2_m3_m6_m4_m5:C(#N)CC(=O)OCC, amount is: 0.0 ;m1_m2_m3_m6_m4_m5:ClC(C(=O)OCC)(C#N)Cl, amount is: 0.0 ;m1_m2_m3_m6_m4_m5:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m6_m4_m5:C(\C=C\C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m6_m4_m5:CCOC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC(C(=O)OCC)(C(CC=O)C)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the procedure for the preparation of ethyl 2-chloro-2-cyano-5-oxopentanoate (Example 1), 37.6 g of ethyl cyanoacetate, 60.5 g of ethyl dichlorocyanoacetate, 350 mL of EtOAc, 1.7 g of K2CO3, and 56 mL of crotonaldehyde were allowed to react for an extended period of time. The title compound was obtained in 34% yield after workup and distillation (b.p. 115° C./1.0 mm Hg). |
Here is a chemical reaction formula: Reactants are m0_m2_m3_m5_m4:ClC1=NC=CC(=C1C(=O)OCC)C, amount is: 0.0 ;m0_m2_m3_m5_m4:[NH4+].[Cl-], amount is: 0.0 ;m1:ClC1=NC=CC=C1C(=O)N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m0_m2_m3_m5_m4:N, amount is: 0.0 ,Catalysts are m0_m2_m3_m5_m4:[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-], amount is: 0.0 MOLE.Products are 0:ClC1=NC=CC(=C1C(=O)N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a manner similar to that described for 2-chloro-3-pyridinecarboxamide in Example 13, the title compound (m.p. 168-170) was prepared in 64% yield from 4 g of ethyl 2-chloro-4-methyl-3-pyridinecarboxylate, 1 g of NH4Cl, 30 mL of concentrated aqueous ammonia, and 0.6 of Bu4NBr. |
Here is a chemical reaction formula: Reactants are m1_m4:ClC1=NC=CC(=C1C(=O)O)C, amount is: 0.0 ;m2:O=S(Cl)Cl, amount is: 0.0 ;m3:N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=NC=CC(=C1C(=O)N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 2-chloro-4-methyl-3-pyridinecarboxylic acid (24.7 g, 157 mmol) and 75 mL of toluene at 70° C. was added 75 mL of SOCl2 (22.6 g, 190 mmol) within a period of 1 hour. The reaction mixture was refluxed for 4 hours and the resulting solution was cooled to room temperature. Dry NH3 gas was introduced at such a rate so as to maintain the internal temperature below 30° C. After removing toluene, the solid residue was washed successively with cold water and methanol, and dried to yield 22.72 g of the title compound (91%, m.p. 168°-170° C.). |
Here is a chemical reaction formula: Reactants are m3_m4:COC(C(CC(C=O)C1=CC=CC=C1)(C#N)Cl)=O, amount is: 0.0 ;m1_m5:P(Cl)(Cl)Cl, amount is: 0.0 ;m2:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m4:CN(C)C=O, amount is: 0.0 ;m1_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=NC=C(C=C1C(=O)OC)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5 g of PCl3 were added to 25 mL of DMF at room temperature. The resulting yellow solution was saturated with anhydrous HCl while keeping the temperature below 90° C. 5 g (18 mmol) of methyl-2-chloro-2-cyano-4-phenyl-5-oxopentanoate in 5 mL DMF were added at 80° C. and the resulting solution heated at 90° C. for 90 min. The reaction mixture was cooled to room temperature, quenched with water, extracted with toluene, dried and distilled to give methyl 2-chloro-5-phenyl-3-pyridine carboxylate. |
Here is a chemical reaction formula: Reactants are m3:C(CCCCC)O, amount is: 0.0 MOLE;m1_m2_m5:C(C)(C)[Si](C(C)C)(C(C)C)Cl, amount is: 0.0 ;m1_m2_m5:N1C=NC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CCCCCC, amount is: 0.0 ;m1_m2_m5:CCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)[Si](OCCCCCC)(C(C)C)C(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 250 ml, three-necked flask was fitted with a large magnetic, egg-shaped stir bar, a small, pressure-equalizing addition funnel, a thermocouple connected to a THERM-O-WATCH®, a reflux condenser, and an argon inlet. This apparatus was dried in an oven overnight at 125° C., assembled hot, and allowed to cool to room temperature in a stream of argon. The flask was charged with 32.46 grams (0.168 mole, 1.01 equivalents) of triisopropylsilyl chloride, 11.69 grams (0.172 mole, 1.03 equivalents) of imidazole, and 100 mls of hexane. 1-Hexanol, 17.03 grams (0.167 mole, 1.00 equivalent), was then added dropwise to the resultant slurry. A very mild exotherm was detected. The total feed time was five minutes. A heavy, white precipitate formed after a few more minutes stirring. The reaction mixture became very hard to stir. Therefore, an additional 25 mls of hexane was added to the reaction. The progress of the reaction was monitored by gas chromatography (GC). An aliquot of the clear supernatant was injected into the GC. The sample at 2.33 hours indicated the conversion to the desired product was 73.0%. The reaction mixture was heated to 40° C. with a heating mantle, controlled by the THERM-O-WATCH®. After stirring overnight at 40° C., the conversion had increased to 87.2%. The temperature was increased to 60° C. After seven hours at 60° C., the conversion was 90.0%. The reaction mixture was heated to reflux overnight, under a blanket of argon. The temperature was decreased to 60° C., and the reaction was analyzed by GC. The conversion was 95.2%. The reaction mixture was held at 60° C. for an additional seven hours, then the reaction mixture was allowed to stir at room temperature over the weekend. The conversion had reached 98.1%. The reaction mixture was transferred to a small, dry, Chemglass pressure filter. The tiltrate was collected in a dry, 500 ml flask. The filter cake was rinsed with additional hexane (2×100 ml). The solvent was removed on the rotary evaporator, with the bath temperature set at 40° C. |
Here is a chemical reaction formula: Reactants are m4:N1C=NC=C1, amount is: 0.0 MOLE;m2:[SiH3]Cl, amount is: 0.0 MOLE;m1_m5:[Si](C)(C)(C(C)(C)C)Cl, amount is: 0.0 ;m3:ClCCCCCCO, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5:C1CCCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OCCCCCCCl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 250 ml, three-necked flask was fitted with a large magnetic, egg-shaped stir bar, a thermocouple, reflux condenser, and an argon inlet. This apparatus was dried in an oven overnight at 125° C., assembled hot, and allowed to cool to room temperature in a stream of argon. The flask was charged with 15.09 grams (0.100 mole, 1.00 equivalents) of t-butyldimethylsilyl chloride, and 100 grams of cyclohexane. The silyl chloride rapidly dissolved, endothermically. 6-Chloro-1-hexanol, 13.96 grams (0.100 mole, 1.00 equivalent) was then weighed into the flask. After stirring at room temperature for fifteen minutes, the reaction mixture appeared hazy. The stirrer was halted, and a second, immiscible layer was observed in the bottom of the flask. Imidazole, 6.81 grams (0.100 mole, 1.00 equivalent) was then added to the reaction mixture. A fine white precipitate rapidly developed. The reaction mixture was stirred at room temperature, and monitored by GC analysis. An aliquot of the clear supernatant was injected into the GC. After five hours, both starting materials were still present, and the conversion to the desired product was 82.2%. The reaction mixture was stirred overnight at room temperature, under a blanket of argon. The sample after 30 hours indicated all the starting material had been consumed, with the formation of a single, higher boiling component. The reaction mixture was transferred to a small, dry, Chemglass pressure filter. The filtrate was collected in a dry, 500 ml flask. The filter cake was rinsed with additional cyclohexane (2×100 ml). The solvent was removed on the rotary evaporator, with the bath temperature set at 40° C. |
Here is a chemical reaction formula: Reactants are m4:Cl.C(C)N(CC)CC, amount is: 0.0 MOLE;m2:[SiH3]Cl, amount is: 0.0 MOLE;m3:ClCCCCCCO, amount is: 0.0 MOLE;m1_m6:[Si](C)(C)(C(C)(C)C)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)N(CC)CC, amount is: 0.0 MOLE;m1_m6:C1CCCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OCCCCCCCl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 250 ml, three-necked flask was fitted with a large magnetic, egg-shaped stir bar, a thermocouple, a small, pressure-equalizing addition funnel, a reflux condenser, and an argon inlet. This apparatus was dried in an oven overnight at 125° C., assembled hot, and allowed to cool to room temperature in a stream of argon. The flask was charged with 16.20 grams (0.108 mole, 1.00 equivalents) of t-butyldimethylsilyl chloride, and 100 grams of cyclohexane. The silyl chloride rapidly dissolved, endothermically. 6-Chloro-1-hexanol, 15.06 grams (0.108 mole, 1.00 equivalent) was then added dropwise in five minutes. Triethylamine, 10.93 grams (0.108 mole, 1.00 equivalent) was then added dropwise to the reaction mixture. An exotherm was noted, and fumes of triethylamine hydrochloride were observed. A fine, white precipitate rapidly developed. The reaction mixture was stirred at room temperature, and monitored by GC analysis. An aliquot of the clear supernatant was injected into the GC. After one and a half hours, both starting materials were still present, and the conversion to the desired product was only 27.8%. The reaction mixture was stirred overnight at room temperature, under a blanket of argon. The sample after 21 hours indicated only a 53.3% conversion to the desired product. After 161.5 hours stirring, the conversion was still only 88.0%. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m6:C(CCC)[Li], amount is: 0.0 ;m1_m2_m3_m6:CN(CCN(C)C)C, amount is: 0.0 ;m1_m2_m3_m6:FC1(OC2=C(O1)C=CC=C2)F, amount is: 0.0 ;m5:Cl, amount is: 0.0 ;m4:CN(C)C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m6:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1=CC(=C2C(=C1)OC(O2)(F)F)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 94.0 g (272 mmol) of n-butyllithium (18.5% in toluene) are added dropwise under a nitrogen atmosphere, at from -15° to -10° C., over a period of 1.5 hours, to 29.5 g (254 mmol) of N,N,N',N'-tetramethylethylenediamine and 40.0 g (253 mmol) of 2,2-difluoro-1,3-benzodioxole in 35 ml of toluene, an orange suspension being formed. 19.7 g (270 mmol) of DMF are then metered in at from -15° to -10° C. over a period of 1/2 hour. The pale yellow suspension is poured at +10° C. onto 346 g (1.105 mol) of 11.6% aqueous hydrochloric acid and the whole is stirred for 1/2 hour to complete the reaction. The aqueous phase is separated off and the organic phase is concentrated by evaporation in a vacuum rotary evaporator at 50° C./200 mbar under nitrogen to yield the desired product. |
Here is a chemical reaction formula: Reactants are m1:FC1(OC2=C(O1)C=CC=C2)F, amount is: 0.0 ;m2_m3_m5:C(CCC)[Li], amount is: 0.0 ;m2_m3_m5:CN(C)CCN(C)C, amount is: 0.0 ;m0_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3_m5:CCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OC(C(C#N)=COCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 7.9 g (50 mmol) of 2,2-difluoro-1,3-benzodioxole are metallated according to Example 2 at -15° C. with 35 ml (55 mmol) of n-butyllithium (1.60 M in hexane) and 6.5 g (55 mmol) of TMEDA in 60 ml of hexane. To the 2,2-difluoro-1,3-benzodioxol-4-yllithium which precipitates there is added at -20° C., over a period of 30 minutes, a solution of 9.3 g (55 mmol) of ethoxymethylenecyanoacetic acid ethyl ester in 30 ml of tetrahydrofuran, an orange-red turbid solution being formed during the reaction, which is exothermic. After stirring for 20 minutes at -15° C., the solution is hydrolysed with 50 ml of 2N hydrochloric acid. The aqueous phase is extracted twice with 80 ml of diethyl ether each time. The organic solutions are washed twice with 50 ml of water each time, dried over MgSO4 and concentrated to dryness by evaporation in a vacuum rotary evaporator. The residue is crystallised from ethanol/water 4:1, affording 10.1 g (72%) of colourless platelets of m.p. 87°-88° C. |
Here is a chemical reaction formula: Reactants are m2:CN(C)CCN(C)C, amount is: 0.0 ;m3:C(CCC)[Li], amount is: 0.0 ;m4_m6:C(C)OC(C(C#N)=COCC)=O, amount is: 0.0 ;m1:FC1(OC2=C(O1)C=CC=C2)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C1(=CC=CC=C1)C, amount is: 0.0 ;m7:O, amount is: 0.0 ;m4_m6:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OC(\C(=C\C1=CC=CC=2OC(OC21)(F)F)\C#N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 40.0 g (253 mmol) of 2,2-difluoro-1,3-benzodioxole in 29.5 g (254 mmol) of TMEDA and 35 ml of toluene are metallated analogously to Example 2c) at from -15° to -10° C. with 106.2 g (307 mmol) of n-butyllithium solution (18.5% in toluene). 52.1 g (308 mmol) of ethoxymethylenecyanoacetic acid ethyl ester in 115 ml of toluene are added to the reaction mixture at from -15° to -10° C. over a period of 2 hours. The resulting suspension is poured, after 20 minutes at +10° C., into 350 ml of water, the aqueous phase is separated off and the organic phase is concentrated by evaporation in a vacuum rotary evaporator to yield the desired product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5:C(CCC)[Li], amount is: 0.0 ;m1_m2_m3_m4_m5:CN(CCN(C)C)C, amount is: 0.0 ;m1_m2_m3_m4_m5:FC1(OC2=C(O1)C=CC=C2)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m2_m3_m4_m5:CCCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1(OC2=C(O1)C=CC=C2[Li])F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 94.0 g (272 mmol) of n-butyllithium (18.5% in toluene) are added dropwise under a nitrogen atmosphere at from -15° to -10° C. to 29.5 g (254 mmol) of N,N,N',N'-tetramethylethylenediamine and 40.0 g (253 mmol) of 2,2-difluoro-1,3-benzodioxole in 35 ml of toluene, n-butane being formed in addition to the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2:CN(CCN(C)C)C, amount is: 0.0 ;m1_m2:C(CCC)[Li], amount is: 0.0 ;m3_m4_m5:FC1(OC2=C(O1)C=CC=C2)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4_m5:C1(=CC=CC=C1)C, amount is: 0.0 ;m3_m4_m5:CCCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1(OC2=C(O1)C=CC=C2[Li])F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 39.3 g (339 mmol) of N,N,N',N'-tetramethylethylenediamine are added dropwise under a nitrogen atmosphere at from -15° to -10° C. to 137.8 g (409 mmol) of n-butyllithium solution (19.0% in toluene). The resulting reaction mixture is added dropwise at from -15° to -10° C. under a nitrogen atmosphere to a solution of 53.3 g (337 mmol) of 2,2-difluoro-1,3-benzodioxole in 46 ml of toluene, n-butane being formed in addition to the title compound. |
Here is a chemical reaction formula: Reactants are m1_m4:IC1=C(C=CC=C1)S(=O)(=O)N, amount is: 0.0 ;m2:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m3:C(CC)N=C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:IC1=C(C=CC=C1)S(=O)(=O)NC(=O)NCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4 g of iodobenzene-sulfonamide and 40 ml of acetone were mixed together and 3.92 g of potassium carbonate were added. The reaction was heated to reflux and 1.46 ml of n-propyl isocyanate were added. The medium was maintained at reflux for 2 hours, and after concentrating, 200 ml of water were added. Then, while cooling the reaction mixture to approximately 0°-5° C., a 2N hydrochloric acid solution was added until a pH of 3 was obtained. After crystallizing from acetone-isopropyl ether, 4.9 g of the expected product melting at 211°-212° C. were obtained. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:B(O)(O)C1=CC=C(C=C1)CN1C(=NC(=C1C(=O)OCC)SC)CCCC, amount is: 0.0 ;m1_m2_m3:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m2_m3:C(CCO)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(CCC)C=1N(C(=C(N1)SC)C(=O)OCC)CC1=CC=C(C=C1)B1OCCO1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1.292 g of ethyl 1-[(4-boronophenyl)-methyl]-2-butyl-4-(methylthio)-1H-imidazole-5-carboxylate of Preparation 3, 25 ml of toluene and 0.710 ml of 1,3 propanediol was stirred at reflux for 4 hours while eliminating the water formed. After evaporating to dryness under reduced pressure, the residue was crystallized hot and cold from heptane, filtered and washed to obtain 1.12 g of the desired product. |
Here is a chemical reaction formula: Reactants are m1_m2:B(O)(O)C1=CC=C(C=C1)CN1C(=NC(=C1C(=O)OCC)SC)CCCC, amount is: 0.0 ;m1_m2:C=1(O)C(O)=CC=CC1, 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:C(CCC)C=1N(C(=C(N1)SC)C(=O)OCC)CC1=CC=C(C=C1)B1OC2=C(O1)C=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using the procedure of Preparation 4, 1 g of ethyl 1-[(4-boronophenyl)-methyl]-2-butyl-4-(methylthio)-1H-imidazole-5-carboxylate and 0.293 g of catechol were reacted to obtain the desired product. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:CC(C)(C)OC(=O)ON=C(C#N)C1=CC=CC=C1, amount is: 0.0 ;m1_m3_m2_m4:Cl.Cl.C(C1=CC=CC=C1)ONCCCCCN, amount is: 21.100000381469727 MILLIMOLE,this reaction does not need reagents,Solvents are m1_m3_m2_m4:C1CCOC1, amount is: 0.0 ;m1_m3_m2_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)ONCCCCCNC(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1 N NaOH (100 mL) was added to (6) (6.01 g, 21.4 mmol), followed by extraction with ether (5×50 mL). After a brine wash (50 mL), solvent was removed to give 4.39 g of (6) as the free amine. BOC-ON (5.10 g, 20.7 mmol ) in distilled THF (100 mL) was added to (6) (free amine, 21.1 mmol) in THF (165 mL) at 0° C. over 30 minutes. The reaction was stirred (0° C. to room temperature) for 24 hours and concentrated in vacuo. Cold 1N NaOH (100 mL) was added, followed by extraction with EtOAc (4×100 mL). The organic layer was washed with cold 1 N NaOH (3×80 mL), cold 0.5M citric acid (100 mL) and brine (2×100 mL). Removal of solvent gave 6.38 g (quantitative) of (7), which was used directly in the next step, as a liquid: NMR δ 1.2-1.7 (m+s, 15 H), 2.66-3.23 (m, 4 H), 4.5 (br s, 1 H), 4.67 (s, 2 H), 7.16-7.34 (m, 5 H) . An analytical sample was purified on a silica gel column, eluting with 15% EtOAc/CHCl3. Anal. calcd. for C17H28N2O3 : C, 66.20; H, 9.15; N, 9.08. Found: C, 66.13; H, 9.10; N, 9.05. |
Here is a chemical reaction formula: Reactants are m3_m1_m2:C(C1=CC=CC=C1)ONCCCCCNC(=O)OC(C)(C)C, amount is: 0.0 ;m3_m1_m2:C1(CCC(=O)O1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m1_m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)ON(C(CCC(=O)O)=O)CCCCCNC(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Pyridine (80 mL) was added to (7) (6.38 g, 20.7 mmol ) and succinic anhydride (3.11 g, 31.1 mmol ) and the reaction was heated under nitrogen at 80°-86° C. for 1.5 hours. Solvent was removed under high vacuum and the residue was dissolved with ether (150 mL) and washed with saturated NaHCO3 (4×50 mL). The aqueous portion was extracted with ether (2×50 mL), cooled to 0° C., acidified with cold 1N HCl (350 mL) and extracted with CHCl] (6×100 mL). A water wash (100 mL), solvent removal and flash column chromatography, eluting with 6% CH3OH/CH2Cl2, gave 7.46 g (88%) of (8) as a solid: mp 93°-94° C., NMR δ 1.2-1.8 (m+s, 16 H), 2.62 (s, 4 H), 2.9-3.2 (m, 2 H), 3.51-3.76 (m, 2 H), 4.8 (s, 2 H), 7.33 (s, 6 H). Anal. calcd. for C21H32N2O6 : C, 61.75; H, 7.90, N, 6.86. Found: C, 61.48; H, 7.90; N, 6.79. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)ON(CCCCCNC(=O)OC(C)(C)C)C(CCC(NCCCCCNOCC1=CC=CC=C1)=O)=O, amount is: 0.0 ;m1_m2_m3:C1(CCC(=O)O1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)ON(C(CCC(=O)O)=O)CCCCCNC(CCC(N(CCCCCNC(=O)OC(C)(C)C)OCC1=CC=CC=C1)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of (9) (2.2 g, 3.48 mmol), succinic anhydride (0.55 g, 5.5 mmol) and pyridine (70 mL) was heated at 81° C. for 2 hours. Solvent was removed in vacuo and cold 1N HCl (100 mL) was added. Extraction was carried out with CHCl3 (6×75 mL), followed by a water wash (100 mL). Solvent removal and flash column chromatography, eluting with 7% MeOH/CH2Cl2, afforded 1.98 g (81%) of (10) as an oil: 300 MHz NMR δ 1.2-1.7 (m+s, 21 H), 2.53 (t, 2 H, J=7), 2.67 (s, 4 H), 2.78-2.86 (m, 2 H), 3.02-3.11 (m, 2 H), 3.22 (q, 2 H, J=6), 3.56-3.77 (m, 4 H), 4.7 (br s, 1 H), 4.83 (s, 2 H), 4.86 (s, 2 H) , 6.73 (br s, 1 H) , 7.38 (s, 10 H) . Anal. calcd. for C37H54N4O9 : C, 63.59; H, 7.79; N, 8.02. Found: C, 63.4 5; H, 7.81; N, 8.07. |
Here is a chemical reaction formula: Reactants are m3_m5:Cl.Cl.C(C1=CC=CC=C1)ONCCCCCN, amount is: 0.0 ;m1_m2_m4:C1=CN(C=N1)C(=O)N2C=CN=C2, amount is: 0.0 ;m1_m2_m4:C(C1=CC=CC=C1)ON(C(CCC(=O)O)=O)CCCCCNC(CCC(N(CCCCCNC(=O)OC(C)(C)C)OCC1=CC=CC=C1)=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:C(Cl)Cl, amount is: 0.0 ;m1_m2_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)NCCCCCN(C(CCC(NCCCCCN(C(CCC(NCCCCCNOCC1=CC=CC=C1)=O)=O)OCC1=CC=CC=C1)=O)=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: CDI (0.188 g, 1.16 mmol) was added to a solution of (10) (0.76 g, 1.09 mmol) in dry CH2Cl2 (45 mL). The solution was cooled to 0° C. after 1 hour and (6) (free amine, 0.240 g, 1.15 mmol) was added by cannula in CH2Cl2 (60 mL) over 5 minutes. The reaction was stirred at 0° C. to room temperature for 24 hours. Solvent was removed in vacuo and dilute brine (100 mL) was added to the residue. Extraction was carried out with EtOAc (5×75 mL), followed by washing with 50 mL of cold 0.5M citric acid, 5% NaHCO3, water and brine. Solvent removal gave 0.87 g (90% ) of (11) which was used directly in the next reaction: NMR δ 1.1-1.8 (m+s, 27 H) , 2.3-3.7 (m, 20 H), 4.5 (br s, 1 H), 4.67 (s, 2 H), 4.82 (s, 4 H), 6.2 (br s, 1 H), 7.2-7.4 (m, 15 H). An analytical sample of (11) was obtained from silica gel column chromatography, eluting with 5% MeOH/CHCl3. Anal. calcd. for C49H72N6O9 : C, 66.19; H, 8.16; N, 9.45. Found: C, 66.18; H, 8.17; N, 9.42. |
Here is a chemical reaction formula: Reactants are m3:C(C)(=O)Cl, amount is: 0.0 ;m1_m2_m4:CCN(CC)CC, amount is: 0.0 ;m1_m2_m4:C(C)(C)(C)OC(=O)NCCCCCN(C(CCC(NCCCCCN(C(CCC(NCCCCCNOCC1=CC=CC=C1)=O)=O)OCC1=CC=CC=C1)=O)=O)OCC1=CC=CC=C1, amount is: 0.0 ,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:C(C)(C)(C)OC(=O)NCCCCCN(C(CCC(NCCCCCN(C(CCC(NCCCCCN(C(C)=O)OCC1=CC=CC=C1)=O)=O)OCC1=CC=CC=C1)=O)=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: NEt3 (0.16 mL, 1.15 mmol) was added to (11) (0.87 g, 0.98 mmol) in CH2Cl2 (40 mL) and the solution was cooled to 0° C. Acetyl chloride (0.074M in CH2Cl2, 14 mL, 1.04 mmol) was added by syringe over 4 minutes and stirring was continued (0° C. to room temperature) for 24 hours. The aqueous phase was extracted with CH2Cl2 (4×50 mL) and the organic phase was washed with 40 mL portions of cold 0.25M citric acid, 5% NaHCO3 and H2O. Solvent removal and flash column chromatography with 60% acetone/hexane gave 0.79 g (87%) of (12) as an oil: 300 MHz NMR δ 1.23-1.69 (m+s, 27 H), 2.09 (s, 3 H), 2.44-2.53 (m, 4 H), 2.76-2.84 (m, 6 H), 3.03-3.24 (m, 6 H), 3.57-3.68 (m, 6 H), 4.7 (br s, 1 H), 4.81 (s, 2 H), 4.85 and 4.86 (2 s, 4 H), 6.35 (br s, 1 H), 7.38 (s, 15 H). Anal. calcd. for C51H74N6O10 : C, 65.78; H, 8.01; N, 9.03. Found: C, 65.89; H, 8.04; N, 8.95. |
Here is a chemical reaction formula: Reactants are m3_m1_m2:C(C)(C)(C)OC(=O)NCCCCCN(C(CCC(NCCCCCN(C(CCC(NCCCCCN(C(C)=O)OCC1=CC=CC=C1)=O)=O)OCC1=CC=CC=C1)=O)=O)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m1_m2:CO, amount is: 0.0 ,Catalysts are m3_m1_m2:[Pd], amount is: 0.0 .Products are 0:C(C)(C)(C)OC(=O)NCCCCCN(C(CCC(NCCCCCN(C(CCC(NCCCCCN(C(C)=O)O)=O)=O)O)=O)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 10% Pd-C (227 mg) was added to a solution of (12) (0.346 g, 0.372 mmol) in MeOH (100 mL). The reaction flask was degassed three times with nitrogen and hydrogen gas was introduced at 1 atm. The mixture was rapidly stirred at room temperature for 20 minutes. After the reaction flask was evacuated and filled with nitrogen several times, the catalyst was filtered through a sintered glass filter (10-15μ) and solids were washed with MeOH. After solvent removal by rotary evaporation, the residue was passed through a short Sephadex LH-20 column, eluting with MeOH. The band was dried to provide 199 mg (81%) of (13) as an amorphous white solid: 300 MHz NMR (d6 -DMSO) δ 1.12-1.53 (m+s, 27 H), 1.95 (s, 3 H), 2.25 (t, 4 H, J=7), 2.52-2.60 (m, 4 H), 2.82-3.03 (m, 6 H), 3.43 (t, 6 H, J=6), 7.4 (m, 1 H), 7.8 (m, 2 H), 9.7 (br s, 3 H). The spectrum was identical to an authentic sample of (13). |
Here is a chemical reaction formula: Reactants are m2_m4_m5:C(C)OC(CCNC(C1=C(C=CC(=C1)OCC1=CC=C(C=C1)C#N)N)=O)=O, amount is: 0.0 ;m1_m3:BrCC(=O)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m4_m5:C(Cl)Cl, amount is: 0.0 ;m2_m4_m5:O, amount is: 0.0 ;m1_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OC(CCNC(C1=C(C=CC(=C1)OCC1=CC=C(C=C1)C#N)NC(CBr)=O)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.44 g (7.15 mmol, 1.1 eq.) bromoacetyl bromide in 10 mL of methylene chloride was added over 10 mins. to a stirred biphasic solution of 2.38 g (6.5 mmol, 1.0 eq.) of N-(5-(4-cyanobenzyloxy)-2-aminobenzoyl)-β-alanine ethyl ester in 100 ml of methylene chloride and 30 mL of water cooled to 0° C. The reaction was complete in 1/2 hr. (TLC, 96 CH2Cl2 :4 MeOH, product Rf =0.71) and was partitioned between dilute aqueous sodium bicarbonate and methylene chloride. The organic phase was dried over sodium sulfate, filtered and concentrated to give 3.11 g (98%) of off white crystals of N-(5-(4-cyanobenzyloxy)-2-(bromoacetyl)aminobenzoyl)-β-alanine ethyl ester which was used unpurified but may be recrystallized from ethyl acetate/hexane. 1H NMR (CDCl3, δTMS) 8.41(1H,d,ArH), 7.60 (4H,abq,ArH), 7.02(2H,d,ArH), 6.98(1H,t,NH), 5.12 (2H,s,ArCH2O),4.16 (2H,q, COOCH2),3.97 (2H,s,CH2Br), 3.68 (2H,Q,NCH2), 2.61 (2H,t,CH2COO), 1.25 (3H,t,CH3). IR (KBr): 3389(NH), 3355(NH), 2226(CN), 1735(ester), 1675,1642(amides),1609,1523,1423,1244,1184,819. MS (FAB,M+H+) cald for C22H22N3O5Br 488.3, found (M+H+) 489. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5_m4_m6:C1(=CC=CC=C1)NC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m5_m4_m6:BrCC=CCBr, amount is: 0.0 ;m1_m2_m3_m5_m4_m6:[I-].[K+], amount is: 0.0 ;m1_m2_m3_m5_m4_m6:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5_m4_m6:O, amount is: 0.0 ,Catalysts are m1_m2_m3_m5_m4_m6:[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:C1(=CC=CC=C1)N(CC=CCN(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A vigorously stirred mixture of diphenylamine (150 g, 0.9 mol), 1,4-dibromobut-2-ene (104 g, 0.49 mol), potassium iodide (8 g, 0.05 mol), tetrabutylammonium bromide (7 g, 0.025 mol), sodium hydroxide (43 g, 1.06 mol) and 150 ml of water is warmed to 60° C. for five hours. The mixture is allowed to cool to room temperature. The solids formed are collected and washed with water. The residue is recrystallized from ethanol to give 69 grams (36% yield) of the title compound as a tan solid melting at 105°-107° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C1(=CC=CC=C1)NC1=CC=CC2=CC=CC=C12, amount is: 0.0 ;m1_m2:BrCC=CCBr, 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:C1(=CC=CC=C1)N(CC=CCN(C1=CC=CC2=CC=CC=C12)C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-phenyl-1-naphthylamine (63 g, 0.29 mol) and 1.4-dibromobut-2-ene (12 g, 0.056 mol) is heated to 70° C. for three days. The resulting reaction mass is allowed to cool and is then extracted with 3×100 ml of hot hexane. The combined hexane extracts are concentrated in vacuo to an oil which is chromatographed (silica gel. 95/5 cyclohexane/diethyl ether) to give an oil. Said oil is then crystallized from ether to give 4.8 g (17.5% yield) of the title compound as a tan solid melting at 140°-142° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)NCC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:C(C)(=O)OCC=CCOC(C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O1CCCC1, amount is: 0.0 ,Catalysts are m4:C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1, amount is: 0.0 .Products are 0:C(C)(=O)OCC=CCN(CC1=CC=CC=C1)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of dibenzylamine (40 g, 0.2 mol) and 2-butene-1,4-diol diacetate (105 g, 0.61 mol) dissolved in 150 ml of tetrahydrofuran (THF) is treated with tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo and the excess 2-butene-1,4-diol diacetate is removed by bulb-to-bulb distillation at 80°-90° C./1 mm. The residue is purified by eluting through a short plug of silica gel (1:1 ethyl acetate:hexanes). 1-Acetoxy-4-dibenzylamino-2-butene is obtained in a yield of 59.2 g (95%). |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)NCC1=CC=CC=C1, amount is: 0.0 MOLE;m1:C(C)(=O)OCC=CCN(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)N(CC=CCN(CC1=CC=CC=C1)CC1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of Example 11 by replacing 1-acetoxy-4-dibenzylamino-2-butene with 1-acetoxy-4-diphenylamino-2-butene and replacing dicyclohexylmethylamine with dibenzylamine, the title compound is obtained as a white solid. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m1_m5_m2_m3:OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OC)\C)OC)C)=O, amount is: 0.0 ;m1_m5_m2_m3:[Si](C)(C)(C(C)(C)C)Cl, amount is: 0.0 ;m1_m5_m2_m3:N1C=NC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m3:CN(C=O)C, 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(/CCC(=O)OC)\C)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To methyl (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (Tetrahedron, 28, 4395, 1972) (10.0 g) in dimethylformamide (75 ml) was added t-butyldimethylsilyl chloride (4.97 g) and imidazole (2.24 g). The mixture was heated at 50° C. for 1 hour, then left at room temperature for 24 hours, then poured into water and extracted with ethyl acetate. The extract was washed twice with water, dried over magnesium sulfate and evaporated under vacuum to give methyl (E) 6-(4-t-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate as a beige solid. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OC)\C)OC)C)=O, amount is: 0.0 ;m1_m4_m2_m3:C(C)(C)N(CC)C(C)C, amount is: 0.0 ;m1_m4_m2_m3:COCCOCCl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CCC(=O)OC)\C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To methyl (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (61.0 g) in methylene chloride (1000 ml) at 0° C. was added diisopropylethylamine (30.4 g) and methoxyethoxymethyl chloride (29.2 g). After 31/2 hours the solution was washed with dilute hydrochloric acid, dried and evaporated to give methyl (E) 6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate as an oil. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OC)\C)OC)C)=O, amount is: 0.0 ;m1_m4_m2_m3:ClCCl, amount is: 0.0 ;m1_m4_m2_m3:N1=CC=CC=C1, amount is: 0.0 ;m1_m4_m2_m3:CO, 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:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC=O)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) 6-(4-t-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (11.0 g) in methanol 125 ml), dichloromethane (125 ml) and pyridine (2 ml) was cooled to -78° C. and a stream of ozonized oxygen was bubbled through. After 45 minutes a blue color developed indicating the presence of unreacted ozone. Dimethyl sulfide (5 ml) was added and the cooling bath was removed. After 16 hours the solution was washed with dilute hydrochloric acid, dilute aqueous sodium bicarbonate and then water, then dried and evaporated. The residue was chromatographed on silica gel, eluting with 2:1 hexane:ethyl acetate, so as to produce 2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)acetaldehyde, mp. 88°-92° C. (ether). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)C/C=C(/CCC(=O)OC)\C, amount is: 0.0 ;m1_m3_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 MOLE;m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)CC=C(CCC(=O)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To methyl (E) 6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (76.0 g) in methanol (300 ml) was added 1N aqueous sodium hydroxide (300 ml). After 11/2 hours the solution was diluted with water, washed twice with ether, then acidified with dilute hydrochloric acid. The acidified solution was extracted with ether, and the extract was dried and evaporated to give (E) 6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid, m.p. 77°-82° C. (etherhexane). |
Here is a chemical reaction formula: Reactants are m1:COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)CC=C(CCC(=O)O)C, amount is: 0.0 MOLE;m0_m2:CCCCCC.C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)CC=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: By following the procedure of part A and substituting methyl (E) 6(4-t-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate with (E) 6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid, there was obtained 2-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-acetaldehyde, m.p. 61°-63° C. (hexane-ethyl acetate). |
Here is a chemical reaction formula: Reactants are m3:[Cl-].[NH4+], amount is: 0.0 ;m1_m4_m2_m5:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC=O)OC)C)=O, amount is: 0.0 ;m1_m4_m2_m5:C(C=C)[Mg]Br, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2_m5:C1CCOC1, amount is: 0.0 ;m1_m4_m2_m5:C1CCOC1, 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(=C1CC(C(=C)C)O)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-acetaldehyde (5.25g) in THF (70 ml) at -70° C. was added 1N 2-propenylmagnesium bromide in THF (19 ml). The solution was kept at -40° C. for 15 minutes, then saturated aqueous ammonium chloride (80 ml) was added. The mixture was extracted with ether, and the extract dried and evaporated, to give 4-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-hydroxy-2-methylbut-1-ene, mp 133°-4° C. (tert-butylmethyl ether/hexane). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC(C(=C)C)O)OC)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(CC)(OC)(OC)OC, amount is: 0.0 ;m1_m2_m3:C(CC)(=O)O, 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(/CC(C(=O)OC)C)\C)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-hydroxy-2-methylbut-1-ene (0.91 g) in trimethyl orthopropionate (25 ml) and propionic acid (0.08 ml) was heated to 110° C. for 2.5 hours. The solvents were evaporated under vacuum to afford methyl (E) 6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,4-dimethyl-4-hexenoate as an oil. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OC)C)\C)OC)C)=O, amount is: 0.0 ;m1_m3_m2_m4:[F-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m2_m4:O1CCCC1, amount is: 0.0 ;m1_m3_m2_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OC)C)\C)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To methyl (E) 6-(4-tert -butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,4-dimethyl-4-hexenoate (0.8 g) in tetrahydrofuran (5 ml) was added 1N tetra-n-butylammonium fluoride in tetrahydrofuran (4 ml). After 10 minutes the solution was diluted with ice water and extracted with ethyl acetate. The extract was dried and evaporated to give methyl (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,4-dimethyl-4-hexenoate as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)O)\C)OC)C)=O, amount is: 0.0 ;m1_m2_m3:CI, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3:CC#N, amount is: 0.0 ,Catalysts are m4:[Ag]=O, amount is: 0.0 MOLE.Products are 0:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C/C=C(/C(CC(=O)OCC)OC)\C)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Ethyl (E) 6-(1,3-dihydro-4-tert-butyldimethylsilyloxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-hydroxy-4-methyl-4-hexenoate (974 mg) was dissolved in a 6:1 mixture of methyl iodide in CH3CN (25 ml). Silver oxide was then added (5.1 g) and the mixture heated at reflux for 24 hr. The mixture was cooled to room temperature and filtered through a bed of celite. The celite was washed with CHICl2 (80 ml) and ethyl acetate (80 ml). The combined organic layers were evaporated to dryness and the residue passed through a flash column (silica gel, hexanes-EtOAc 8:2) to afford 601 mg (60%) of ethyl (E) 6-(1,3-dihydro-4-tert-butyldimethylsilyloxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5yl)-3-methoxy-4-methyl-4-hexenoate the product as a colorless oil. |
Here is a chemical reaction formula: Reactants are m3_m7:C(C)(C)[C@H]1N(C(OC1)=O)C(CC)=O, amount is: 0.0 ;m1_m5_m2_m6:C(CCC)[Li], amount is: 0.0 MOLE;m1_m5_m2_m6:C(C)(C)NC(C)C, amount is: 0.0 ;m4_m8:COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)CC=C(CCC(=O)O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m7:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:CCCCCC, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1, amount is: 0.0 ;m4_m8:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)CCC(C[C@@H](C(=O)N1C(OC[C@H]1C(C)C)=O)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.38 molar n-butyllithium in hexane (11.8 ml) was added to diisopropylamine (2.45 ml) in tetrahydrofuran (50 ml) at -10° C. After 20 minutes, the solution was cooled to -78° C., and a solution of (R)-4-isopropyl-3-propionyl-2-oxazolidinone [prepared as described in J. Am. Chem. Soc., 103:2127 (1981)](3.23 g) in tetrahydrofuran (10 ml) was added. After 30 minutes (E) 4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-methylbut-2-enyl bromide (2.54 g) in tetrahydrofuran (12 ml) was added. The reaction temperature was allowed to reach -10° C. slowly, then maintained at that temperature for 3 hours. The reaction was quenched with 10% aqueous ammonium chloride then extracted with ethyl acetate. The extract was washed with 10% hydrochloric acid, dilute aqueous sodium bicarbonate and water, then dried and evaporated. The residue was chromatographed on silica gel, eluting with 2:1 hexane:acetone, to yield (E) 3-[6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-(S),4-dimethylhexanoyl)-4-(R)-isopropyl-2-oxazolidinone as an oil. |
Here is a chemical reaction formula: Reactants are m3:COC1=C(C(=C2C(OCC2=C1C)=O)OCOCCOC)CCC(C[C@@H](C(=O)N1C(OC[C@H]1C(C)C)=O)C)C, amount is: 0.0 ;m1_m4_m2:COP(=O)(OC)CC(=O)OCC, amount is: 0.0 ;m1_m4_m2:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COCCOCOC1=C2C(OCC2=C(C(=C1C/C=C(/CC(C(=O)OCC)P(=O)(OC)OC)\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 ethyl dimethylphosphonoacetate (135 mg) in DMF (5 ml) at 0° was added 50% NaH/oil (33 mg), and the mixture stirred for 10 minutes. (E) 4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-methylbut-2-enyl bromide (600 mg) was added at the same temperature and allowed to reach room temperature in 30 minutes. The reaction was poured onto water and extracted with EtOAc. The organic layers were washed with water, dried over sodium sulfate, and evaporated to give the crude product which was purified by flash chromatography (CH2Cl2 followed by BtOAc) to obtain ethyl (E) 6-(4-methoxyethoxymethoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-(dimethylphosphono)-4-methyl-4-hexenoate as an oil. |
Here is a chemical reaction formula: Reactants are m3_m1_m2:C(CC)(=O)O, amount is: 0.0 ;m3_m1_m2:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1CC(C(=C)C)O)OC)C)=O, amount is: 0.0 ;m3_m1_m2:COC(CCCBr)(OC)OC, 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:BrCCC(C(=O)OC)CC(=CCC=1C(=C2C(OCC2=C(C1OC)C)=O)O[Si](C)(C)C(C)(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of trimethyl 4-bromoorthobutyrate (20 ml), propionic acid (0.22 ml) and 4-(4-tert -butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-hydroxy-2-methylbut-1-ene (3.18 g) was heated at 110° C. in a three-necked flash with a slow nitrogen stream passing over the reaction mixture. After 1 hr 40 min the excess orthoester was removed in vacuo at 55° C. Flash chromatography of the residue on silica gel eluting with 20-30% ethyl acetate/hexane gave methyl 2-(2-bromoethyl)-6-(4-t -butyldimethylsiloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl -hex-4-enoate (2.66 g). |
Here is a chemical reaction formula: Reactants are m0_m2_m3_m6:C(C)(C)NC(C)C, amount is: 0.0 ;m0_m2_m3_m6:C(CCC)[Li], amount is: 0.0 ;m4_m7_m5:BrCCC(C(=O)OC)CC(=CCC=1C(=C2C(OCC2=C(C1OC)C)=O)O[Si](C)(C)C(C)(C)C)C, amount is: 0.0 ;m4_m7_m5:[Li+].CC(C)[N-]C(C)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m0_m2_m3_m6:C1CCOC1, amount is: 0.0 ;m4_m7_m5:C1CCOC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)(C)[N-]C(C)C.[Li+];0:COC(=O)C1(CC1)CC(=CCC=1C(=C2C(OCC2=C(C1OC)C)=O)O[Si](C)(C)C(C)(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of lithium diisopropyl amide was prepared from diisopropyl amine (2.24 ml) and n-butyllithium (6.4 ml, 2.5N) in THF (60 ml) and cooled to -70° C. Methyl 2-(2-bromoethyl)-6-(4-t-butyldimethylsiloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-hex-4-enoate (2.66 g) in THF (12 ml was added to the LDA solution over 2 min. The reaction mixture was stirred for 50 min at -65° C. to -50° C. and quenched in water. Extraction with ethyl acetate and flash chromatography (silica gel, 20-30% ethyl acetate/hexane) gave 1-[4-(4-t-butyldimethylsiloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-methyl-but-2-enyl]cyclopropane carboxylic acid methyl ester (1.34 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3_m5:[Si](C)(C)(C(C)(C)C)OC1=C2C(OCC2=C(C(=C1C[C@H](OC(NC[C@@]1(CC=CC=C1)C)=O)C1=CCCC1)OC)C)=O, amount is: 0.0 ;m1_m2_m4_m3_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m4_m3_m5:Cl[SiH](Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(C)(=O)OCC, amount is: 0.0 ;m1_m2_m4_m3_m5:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m2_m4_m3_m5:C1(=CC=CC=C1)C, 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@H](O)C1=CCCC1)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1-{2-[4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl]-1-(S)-[N-(1-(R)-methylbenzyl)carbamoyloxy]eth-1-yl}cyclopent-1-ene (9.0 g) and triethylamine (4.6 ml) in toluene (60 ml) was added trichlorosilane (2.5 ml) dropwise in toluene (20 ml). After addition, the reaction was submerged in an oil bath pre-heated to 110° C. and stirred for 15 minutes, then cooled to room temperature. The reaction was diluted with ethyl acetate (500 ml) and washed sequentially with aqueous ammonium chloride, dilute hydrochloric acid, aqueous sodium bicarbonate, brine, then dried over magnesium sulfate and evaporated onto 90 g of silica gel. This was placed on top of a silica gel column and eluted with 4:1 hexane:ethyl acetate to afford the product 1-[2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-1-(S)-hydroxyeth-1-yl]cyclopent-1-ene, m.p. 112.0°-112.7° C. (ethyl acetate), [α]D =33.11 (CH3OH). |