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Here is a chemical reaction formula: Reactants are m1_m3_m4:C(=O)(OCC)C1CC=2C(=CSC2)C1, amount is: 0.0 ;m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4:C(C)O, amount is: 0.0 ;m1_m3_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1CC=2C(=CSC2)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carboethoxy)-2,4,5,6-tetrahydrocyclopenta[c]thiophene (6.68 g, 34.1 mmol) in ethanol (95%, 150 mL) and water (75 mL). Add potassium hydroxide (9.5 g, 0.17 mol) and stir at room temperature for 1 hour. Partition between water (150 mL) and ethyl ether (2×150 mL). Acidifythe aqueous phase with hydrochloric acid to pH 1. Extract with methylene chloride (2×150 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 5-(carboxy)-2,4,5,6-tetrahydrocyclopenta[c]thiophene. |
Here is a chemical reaction formula: Reactants are m2_m3:COC(C)(C)OC, amount is: 0.0 ;m2_m3:S(O)(O)(=O)=O, amount is: 0.0 ;m1_m4:C(=O)(O)C1CC=2C(=CSC2)C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1CC=2C(=CSC2)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carboxy)-2,4,5,6-tetrahydrocyclopenta[c]thiophene (3.95 g, 23.5mmol) in methanol (60 mL) and treat with dimethoxypropane (5.8 mL, 47 mmol)and sulfuric acid (0.8 mL). Stir at room temperature for 1 day. Evaporate the solvent in vacuo, dilute with methylene chloride (75 mL) and wash withsaturated sodium hydrogen carbonate (35 mL). Extract the aqueous phase withmethylene chloride (30 mL), wash combined organics with brine (30 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and pass through aplug of silica gel to give 5-(carbomethoxy)-2,4,5,6-tetrahydro-cyclopenta[c]thiophene. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[K+], amount is: 0.0 ;m1_m3_m4_m5:C(=O)(OC)C1(CC=2C(=CSC2)C1)SCC1=CC=C(C=C1)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4_m5:C(C)O, amount is: 0.0 ;m1_m3_m4_m5:O, amount is: 0.0 ;m1_m3_m4_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1(CC=2C(=CSC2)C1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carbomethoxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydro-cyclopenta[c]thiophene (1.14 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 23 mmol) and stir at room temperature for 1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate theaqueous phase and acidify with cold concentrated hydrochloric acid. Extractwith methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give 5-(carboxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydrocyclopenta[c]thiophene. |
Here is a chemical reaction formula: Reactants are m1_m4:C(C)(C)(C)OC(=O)NCCNC(C(F)(F)F)=O, amount is: 0.0 ;m3:C(C=C)Br, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CN(C=O)C, amount is: 0.0 ;m5:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)NCCN(CC=C)C(C(F)(F)F)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)ethylenediamine (562mg, 100%). |
Here is a chemical reaction formula: Reactants are m1_m3:C(C)(C)(C)OC(=O)NCCN(CC=C)C(C(F)(F)F)=O, amount is: 1.9500000476837158 MILLIMOLE;m2:FC(C(=O)O)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C(=O)O)(F)F.FC(C(=O)N(CCN)CC=C)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve N-(t-butyloxycarbonyl)--N'-(trifluoroacetyl)--N'-(allyl)-ethylenediamine (1.95 mmol) in methylene chloride (7 mL) and add trifluoroacetic acid (2.6mL). Stir at room temperature for 1 hour then evaporate the solvent in vacuo to give N'-(trifluoroacetyl)--N'-(allyl)-ethylenediamine trifluoroacetate. |
Here is a chemical reaction formula: Reactants are m5_m2_m3:O, amount is: 0.0 ;m5_m2_m3:O1CCCC1, amount is: 0.0 ;m1:C(=O)(OCC)C(C)(C)SCC1=CC=C(C=C1)OC, amount is: 0.0 ;m4:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C(C)(C)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-(carboethoxy)-2-(4-methoxybenzylthio)propane (1.05 g, 3.91 mmol)in a mixture of 95% ethanol (18 mL), water (9 mL) and tetrahydrofuran (10 mL). Add potassium hydroxide (1.4 g, 25 mmol) and stir at room temperaturefor 2 hours then at 55° C. for 1 hour. Evaporate the solvent in vacuo and partition between water (50 mL) and ether (50 mL). Acidify to pH1 with concentrated hydrochloric acid and extract into methylene chloride (50 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give 2-(carboxy)-2-(4-methoxybenzylthio)propane as a tan solid (763 mg). |
Here is a chemical reaction formula: Reactants are m2:O=[O+][O-], amount is: 0.0 MOLE;m1_m3_m4:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)NCCCC1=CC=CC=C1)CCC=C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4:C(Cl)Cl, amount is: 0.0 ;m1_m3_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)NCCCC1=CC=CC=C1)CCC=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-hexenylamine (1.2 g, 3.19 mmol) in methylene chloride (40 mL) and methanol (4 mL) and cool to -78° C. under a nitrogen atmosphere. Treat with ozone until a blue color persists, degas with nitrogen for 20 minutes and add pyridine (0.2 mL). Quench with dimethylsulfide (4 mL) and stir overnight at room temperature. Dilute with methylene chloride (75 mL) and wash with 5% sulfuric acid (40 mL) and brine (40 mL) . Dry (Na2SO4), evaporate the solvent in vacuo and purify by chromatography (hexane/ethyl acetate) to give 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl-5-oxo-pentylamine as a white solid (972 mg, 80%). |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:C1C(CC2=CC=CC=C12)C(=O)O, amount is: 0.0 ;m1_m4_m2_m3:COC(C)(C)OC, amount is: 0.0 ;m1_m4_m2_m3:S(O)(O)(=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1CC2=CC=CC=C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-indancarboxylic acid (3.82 g, 23.5 mmol) in methanol (60 mL) andtreat with dimethoxypropane (5.8 mL, 47 mmol) and sulfuric acid (0.8 mL). Stir at room temperature for 6 days. Evaporate the solvent in vacuo, dilute with methylene chloride (75 mL) and wash with saturated sodium hydrogen carbonate (35 mL). Extract the aqueous phase with methylene chloride (30 mL), wash combined organics with brine (30 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and pass through a plug of silica gel to give 2-(carbomethoxy)indan as a yellow oil (3.98 g, 96%). |
Here is a chemical reaction formula: Reactants are m2:[OH-].[K+], amount is: 0.0 ;m1_m3_m4_m5:C(=O)(OC)C1(CC2=CC=CC=C2C1)SCC1=CC=C(C=C1)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4_m5:C(C)O, amount is: 0.0 ;m1_m3_m4_m5:O, amount is: 0.0 ;m1_m3_m4_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1(CC2=CC=CC=C2C1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-(carbomethoxy)-2-(4-methoxybenzylthio)indan (2.20 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 23 mmol) and stir at room temperature for1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate the aqueous phase and acidify with cold concentrated hydrochloric acid. Extract with methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify bysilica gel chromatography (2:1 hexane/ethyl acetate) to give 2-carboxy-2-(4-methoxybenzylthio)indan as a yellow solid (0.48 g, 43%). |
Here is a chemical reaction formula: Reactants are m1_m5:C(CC(=O)OCC)(=O)OCC, amount is: 0.0 ;m3:BrCC=1C(=CC=CC1)CBr, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m4:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OCC)C1(CC2=CC=CC=C2C1)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve diethyl malonate (7.6 mL, 50 mmol) in anhydrous tetrahydrofuran (500 mL) and place under an argon atmosphere. Cool to 5° C., add sodium hydride (1.2 g, 50 mmol) and stir briefly until homogeneous. Add α,α'-dibromo-o-xylene (13.2 g, 50 mmol) and stir an additional15 minutes. Add additional sodium hydride (1.2 g, 50 mmol) and stir for 16 hours while warming to room temperature. Filter, evaporate the solvent in vacuo and purify by silica gel chromatography (1:1 methylene chloride/hexane) to give 2,2-dicarboethoxy-indan (9.64 g, 74%). |
Here is a chemical reaction formula: Reactants are m1_m3:C(=O)(OCC)C1(CC2=CC=CC=C2C1)C(=O)OCC, amount is: 0.0 ;m2:[OH-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1CC2=CC=CC=C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2,2-dicarboethoxy-indan (5.67 g, 21.7 mmol) in ethanol (150 mL). Add 1N lithium hydroxide (50 mL) and stir overnight at room temperature. Reflux for 1 hour and concentrate the solution in vacuo. Partition betweenethyl acetate and 6N hydrochloric acid. Separate the organic phase and washwith brine. Dry (MgSO4) and evaporate the solvent in vacuo to give an off-white solid. Distill (120°-160° C. @ 0.2-0.5 mmHg) to give 2-carboxy-indan (2.5 g, 71%). |
Here is a chemical reaction formula: Reactants are m1_m2:C(=O)(O)C1CC2=CC=CC=C2C1, amount is: 0.0 ;m1_m2:CO, 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(=O)(OC)C1CC2=CC=CC=C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-carboxy-indan (2.5 g, 15.4 mmol) in methanol and cool to 0° C. Saturate with hydrochloride gas then add 2,2-dimethoxypropane(2-3 mL). Stir overnight then evaporate the solvent in vacuo. Purify by silica gel chromatography (2:1 methylene chloride/hexane) to give 2-carbomethoxy-indan as a water white oil. (2.04 g, 75%). |
Here is a chemical reaction formula: Reactants are m2:[OH-].[Li+], amount is: 0.0 ;m1_m3:C(=O)(OC)C1(CC2=CC=CC=C2C1)CSC(C)(C)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:C(=O)(O)C1(CC2=CC=CC=C2C1)CSC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-carbomethoxy-2-(t-butyl)thiomethyl-indan (557 mg, 2.0 mmol) in methanol (15 mL) and add 1N lithium hydroxide (3.5 mL). Warm briefly to effect solution then stir at room temperature under an argon atmosphere for 1 hour. Reflux for 6 hours, concentrate in vacuo to a volume of 3 mL and dilute to a volume of 15 mL with water. Wash with methylene chloride and acidify and aqueous phase with excess 2N hydrochloric acid. After 5 minutes, collect the resulting white precipitate by filtration and dry to give 2-carboxy-2-(t-butyl)thiomethyl-indan (506 mg, 96%); mp 158°-163° C. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[K+], amount is: 0.0 ;m1_m3_m4_m5:C(=O)(OC)C1(CCCC1)SCC1=CC=C(C=C1)OC, amount is: 3.299999952316284 MILLIMOLE,this reaction does not need reagents,Solvents are m1_m3_m4_m5:C(C)O, amount is: 0.0 ;m1_m3_m4_m5:O, amount is: 0.0 ;m1_m3_m4_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1(CCCC1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 1-(carbomethoxy)-1-(4-methoxylbenzylthio)cyclopentane (3.3 mmol) in 95% ethanol (18 mL), water (9 mL), and tetrahydrofuran (10 mL). Treat with potassium hydroxide (0.91 g, 16 mmol). Stir at room temperature for 2hours and evaporate the solvent in vacuo. Partition between water (50 mL) and ethyl ether (30 mL). Acidify the aqueous phase with cold concentrated hydrochloric acid and extract with methylene chloride (50 mL). Dry (MgSO4) and evaporate the solvent in vacuo to give 1-(carboxy)-1-(4-methoxybenzylthio)cyclopentane as a pale yellow oil (483 mg, 72%). |
Here is a chemical reaction formula: Reactants are m1_m3_m4:C(=O)(OCC)C1CC=2C(=COC2)C1, amount is: 0.0 ;m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4:C(C)O, amount is: 0.0 ;m1_m3_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1CC=2C(=COC2)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carboethoxy)-2,4,5,6-tetrahydro-cyclopenta[c]furan (6.2 g, 34.1mmol) in ethanol (95%, 150 mL) and water (75 mL). Add potassium hydroxide (9.5 g, 0.17 mol) and stir at room temperature for 1 hour. Partition between water (150 mL) and ethyl ether (2×150 mL). Acidify the aqueous phase with hydrochloric acid to pH 1. Extract with methylene chloride (2×150 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 5-(carboxy)-2,4,5,6-tetrahydro-cyclopenta[c ]furan. |
Here is a chemical reaction formula: Reactants are m1_m4:C(=O)(O)C1CC=2C(=COC2)C1, amount is: 0.0 ;m2_m3:COC(C)(C)OC, amount is: 0.0 ;m2_m3:S(O)(O)(=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1CC=2C(=COC2)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carboxy)-2,4,5,6-tetrahydro-cyclopenta[c]furan (3.6 g, 23.5 mmol) in methanol (60 mL) and treat with dimethoxypropane (5.8 mL, 47 mmol) and sulfuric acid (0.8 mL). Stir at room temperature for 1 day. Evaporate the solvent in vacuo, dilute with methylene chloride (75 mL) andwash with saturated sodium hydrogen carbonate (35 mL). Extract the aqueous phase with methylene chloride (30 mL), wash combined organics with brine (30 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and pass through a plug of silica gel to give 5-(carbomethoxy)-2,4,5,6-tetrahydro-cyclopenta[c]furan. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[K+], amount is: 0.0 ;m1_m3_m4_m5:C(=O)(OC)C1(CC=2C(=COC2)C1)SCC1=CC=C(C=C1)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4_m5:C(C)O, amount is: 0.0 ;m1_m3_m4_m5:O, amount is: 0.0 ;m1_m3_m4_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1(CC=2C(=COC2)C1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carbomethoxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydro-cyclopenta[c]furan (1.08 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 23 mmol) and stir at room temperature for 1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate theaqueous phase and acidify with cold concentrated hydrochloric acid. Extractwith methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give 5-(carboxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydro-cyclopenta[c]furan. |
Here is a chemical reaction formula: Reactants are m1_m3_m4:C(=O)(OCC)C1CC=2C(=CSC2)C1, amount is: 0.0 ;m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4:C(C)O, amount is: 0.0 ;m1_m3_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1CC=2C(=CSC2)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carboethoxy)-2,4,5,6-tetrahydro-cyclopenta[c]thiophene (6.68 g,34.1 mmol) in ethanol (95%, 150 mL) and water (75 mL). Add potassium hydroxide (9.5 g, 0.17 mol) and stir at room temperature for 1 hour. Partition between water (150 mL) and ethyl ether (2×150 mL). Acidifythe aqueous phase with hydrochloric acid to pH 1. Extract with methylene chloride (2×150 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 5-(carboxy)-2,4,5,6-tetrahydro-cyclopenta[c]thiophene. |
Here is a chemical reaction formula: Reactants are m2_m3:COC(C)(C)OC, amount is: 0.0 ;m2_m3:S(O)(O)(=O)=O, amount is: 0.0 ;m1_m4:C(=O)(O)C1CC=2C(=CSC2)C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1CC=2C(=CSC2)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carboxy)-2,4,5,6-tetrahydro-cyclopenta[c]thiophene (3.95 g, 23.5 mmol) in methanol (60 mL) and treat with dimethoxypropane (5.8 mL, 47mmol) and sulfuric acid (0.8 mL). Stir at room temperature for 1 day. Evaporate the solvent in vacuo, dilute with methylene chloride (75 mL) andwash with saturated sodium hydrogen carbonate (35 mL). Extract the aqueous phase with methylene chloride (30 mL), wash combined organics with brine (30 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and pass through a plug of silica gel to give 5-(carbomethoxy)-2,4,5,6-tetrahydro-cyclopenta[c]thiophene. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[K+], amount is: 0.0 ;m1_m3_m4_m5:C(=O)(OC)C1(CC=2C(=CSC2)C1)SCC1=CC=C(C=C1)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m4_m5:C(C)O, amount is: 0.0 ;m1_m3_m4_m5:O, amount is: 0.0 ;m1_m3_m4_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C1(CC=2C(=CSC2)C1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 5-(carbomethoxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydro-cyclopenta[c]thiophene (1.14 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 23 mmol) and stir at room temperature for 1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate theaqueous phase and acidify with cold concentrated hydrochloric acid. Extractwith methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give 5-(carboxy)-5-(4-methoxybenzylthio)-2,4,5,6-tetrahydro-cyclopenta[c]thiophene. |
Here is a chemical reaction formula: Reactants are m1_m4:C(C)(C)(C)OC(=O)NCCNC(C(F)(F)F)=O, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m3:C(C=C)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CN(C=O)C, amount is: 0.0 ;m5:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)NCCN(CC=C)C(C(F)(F)F)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-ethylenediamine (500 mg, 1.95 mmol) in anhydrous dimethylformamide (10 mL), cool to 0° C. and treat with sodium hydride (56 mg, 1.85 mmol, 80% dispersion in mineral oil). Stir for 15 minutes and add allyl bromide (0.25 mL, 2.9 mmol). Stir for 2.5 hours, dilute with ethyl acetate (50 mL) and extract with water (25 mL). Separate the organic phase and wash with brine (2×20 mL). Extract the combined aqueous phases with ethyl acetate (2×5 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (2:1 hexane/ethyl acetate to 3:2 hexane/ethyl acetate) to give N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)-ethylenediamine (562 mg, 100%). |
Here is a chemical reaction formula: Reactants are m2:FC(C(=O)O)(F)F, amount is: 0.0 ;m1_m3:C(C)(C)(C)OC(=O)NCCN(CC=C)C(C(F)(F)F)=O, amount is: 1.9500000476837158 MILLIMOLE,this reaction does not need reagents,Solvents are m1_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C(=O)O)(F)F.FC(C(=O)N(CCN)CC=C)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve N-(t-butyloxycarbonyl)-N'-(trifluoroacetyl)-N'-(allyl)-ethylenediamine (1.95 mmol) in methylene chloride (7 mL) and add trifluoroacetic acid (2.6mL). Stir at room temperature for 1 hour then evaporate the solvent in vacuo to give N'-(trifluoroacetyl)-N'-(allyl)-ethylenediamine trifluoroacetate. |
Here is a chemical reaction formula: Reactants are m4:[OH-].[K+], amount is: 0.0 ;m1:C(=O)(OCC)C(C)(C)SCC1=CC=C(C=C1)OC, amount is: 0.0 ;m5_m2_m3:O, amount is: 0.0 ;m5_m2_m3:O1CCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)C(C)(C)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-(carboethoxy)-2-(4-methoxybenzylthio)propane (1.05 g, 3.91 mmol)in a mixture of 95% ethanol (18 mL), water (9 mL) and tetrahydrofuran (10 mL). Add potassium hydroxide (1.4 g, 25 mmol) and stir at room temperaturefor 2 hours then at 55° C. for hour. Evaporate the solvent in vacuo and partition between water (50 mL) and ether (50 mL). Acidify to pH 1 with concentrated hydrochloric acid and extract into methylene chloride (50 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give 2-(carboxy)-2-(4-methoxybenzylthio)propane as a tan solid (763 mg). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:CC1=C(C(=O)O)C=CC=C1C, amount is: 0.0 ;m1_m2_m3_m5:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m1_m2_m3_m5:CN(C=O)C, amount is: 0.0 ;m4_m6_m7:Cl.Cl.NC1CN2CCC1CC2, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(Cl)Cl, amount is: 0.0 ;m4_m6_m7:C1(=CC=CC=C1)C, amount is: 0.0 ;m4_m6_m7:[OH-].[Na+], amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N12CC(C(CC1)CC2)NC(C2=C(C(=CC=C2)C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2,3-dimethylbenzoic acid (5.0 g; 33.3 mmol), oxalyl chloride (40.0 mmol, 3.5 mL) and dimethylformamide (0.1 mL) were dissolved in methylene chloride (100 mL). The mixture was stirred at room temperature for 1 hour and then concentrated under reduced pressure. A solution of the concentrate in toluene (100 mL) was added dropwise to a stirred solution of (RS)-3-amino-1-azabicyclo[2.2.2]octane dihydrochloride (7.0 g; 35 mmol)in toluene (50 mL) and NaOH (2.0N, 50 mL) at 0° C. The reaction mixture was maintained at 0° C. and stirred for 30 minutes. The aqueous layer was extracted with of toluene (2×50 mL) and the combined organic layers dried over magnesium sulfate. Removal of the solvent under reduced pressure gave (RS)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2,3-dimethylbenzamide as a white solid (5.5 g, 25.4 mmol), m.p. 160°-161° C. The hydrochloride salt is prepared from ethanol-hydrogen chloride. |
Here is a chemical reaction formula: Reactants are m3:N[C@@H]1CN2CCC1CC2, amount is: 0.0 MOLE;m1:ClC=1C(=C(C(=O)O)C=CC1)C, amount is: 0.0 MOLE;m2:NC1CN2CCC1CC2, 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:N12C[C@H](C(CC1)CC2)NC(C2=C(C(=CC=C2)Cl)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Proceeding as in Example 1, Method A, but replacing 2,3-dimethylbenzoic acid with 3-chloro-2-methylbenzoic acid and (RS)-3-amino-1-azabicyclo[2.2.2]octane with (S)-3-amino-1-azabicyclo[2.2.2]octane gave (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-chloro-2-methylbenzamide. |
Here is a chemical reaction formula: Reactants are m3:N[C@@H]1CN2CCC1CC2, amount is: 0.0 MOLE;m2:NC1CN2CCC1CC2, amount is: 0.0 MOLE;m1:C(C1=CC=CC=C1)C1=C(C(=O)O)C=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:N12C[C@H](C(CC1)CC2)NC(C2=C(C=CC=C2)CC2=CC=CC=C2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Proceeding as in Example 1, Method A, but replacing 2,3-dimethyl benzoic acid with 2-benzylbenzoic acid and (RS)-3-amino-1-azabicyclo[2.2.2]octane with (S)-3-amino-1-azabicyclo[2.2.2]octane gave (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-benzylbenzamide. |
Here is a chemical reaction formula: Reactants are m2:NC1CN2CCC1CC2, amount is: 0.0 MOLE;m3:N[C@@H]1CN2CCC1CC2, amount is: 0.0 MOLE;m1:C(CCC)C1=C(C(=O)O)C=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:N12C[C@H](C(CC1)CC2)NC(C2=C(C=CC=C2)CCCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Proceeding as in Example 1, Method A, but replacing 2,3-dimethyl benzoic acid with 2-butylbenzoic acid and (RS)-3-amino-1-azabicyclo[2.2.2]octane with (S)-3-amino-1-azabicyclo[2.2.2]octane gave (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-butylbenzamide. |
Here is a chemical reaction formula: Reactants are m3:COC=1C(=C(C(=O)OC)C=CC1)C, amount is: 0.0 ;m1_m4_m2_m5:C[Al](C)C, amount is: 0.800000011920929 MILLIMOLE;m1_m4_m2_m5:N[C@@H]1CN2CCC1CC2, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m4_m2_m5:C1(=CC=CC=C1)C, amount is: 0.0 MOLE;m1_m4_m2_m5:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N12C[C@H](C(CC1)CC2)NC(C2=C(C(=CC=C2)OC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of trimethylaluminum (0.8 mmol) in toluene was slowly added to asolution of (S)-3-amino-1-azabicyclo[2.2.2]octane (0.1 g; 0.8 mmol) in toluene (5.0 mL) and the mixture stirred for 15 minutes. A solution of methyl 3-methoxy-2-methylbenzoate (0.1 g; 0.55 mmol) in toluene (2 mL) wasadded and the reaction mixture heated to reflux until, as indicated by thin-layer chromatography, the reaction had finished. The mixture was cooled to 0° C. and then carefully quenched with water (0.4 mL). The reaction mixture was stirred for an additional 30 minutes and then filtered washing with ethyl acetate (2×20 mL). Removal of the solvent from the combined filtrate gave (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-methoxy-2-methylbenzamide as a whitesolid (0.19 g, 0.686 mmol). Preparation of the hydrochloride salt from ethanol-hydrogen chloride gave (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-methoxy-2-methylbenzamide hydrochloride, m.p. 259°-261° C., [α]D25 -13.8° (c=0.16, H2O). |
Here is a chemical reaction formula: Reactants are m3:NC1CN2CCC1CC2, amount is: 0.0 MOLE;m1:C(C)C1=C(C(=O)OCC)C=CC=C1C, amount is: 0.0 MOLE;m2:N[C@@H]1CN2CCC1CC2, 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:N12CC(C(CC1)CC2)NC(C2=C(C(=CC=C2)C)CC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Proceeding as in Example 1, Method B, but replacing methyl 3-methoxy-2-methylbenzoate with ethyl 2-ethyl-3-methylbenzoate and (S)-3-amino-1-azabicyclo[2.2.2]octane with (RS)-3-amino-1-azabicyclo[2.2.2]octane gave (RS)-N-(1-azabicyclo[2.2.2]oct-3-yl)-2-ethyl-3-methylbenzamide, m.p. 125° C. |
Here is a chemical reaction formula: Reactants are m3:CN(C=O)C, amount is: 0.0 ;m1_m5_m2_m6:C(CCC)[Li], amount is: 2.200000047683716 MILLIMOLE;m1_m5_m2_m6:N12C[C@H](C(CC1)CC2)NC(C2=C(C(=CC=C2)OC)C)=O, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2_m6:CCCCCC, amount is: 0.0 MOLE;m1_m5_m2_m6:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N12C[C@H](C(CC1)CC2)N2C(C1=CC=CC(=C1C=C2)OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of n-butyllithium (2.2 mmol) in hexane was added in a dropwise fashion to a stirred solution of (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-methoxy-2-methylbenzamide (0.24 g, 0.87 mmol), from Example 1, Method B, in dry tetrahydrofuran (1.0 mL) at -70° C. The mixture was maintained at -10° C. and stirred for 1 hour. The mixture was then cooled to -70° C. and dimethylformamide (0.1 mL) added. The reaction mixture was allowed to warmto room temperature over 1.5 hours, then cooled to 0° C. and acidified with aqueous hydrochloric acid (10%). The layers were separated and the aqueous phase was washed with ethyl acetate. The aqueous layer wasthen made basic with aqueous sodium hydroxide (10N) and extracted with ethyl acetate (3×50 mL). The combined organic phase was dried over anhydrous sodium sulfate and filtered. Evaporation of solvents gave (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-5-methoxy-1 (2H)-isoquinolinone as a white solid (0.23 g, 0.804 mmol). Preparation of the hydrochloride salt from ethanol-hydrogen chloride gave (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-5-methoxyl-1(2H)-isoquinolinone hydrochloride, m.p. 275°-277° C., [α]D25 -106.7° (c=0.30, H2O). |
Here is a chemical reaction formula: Reactants are m2_m5:[H][H], amount is: 0.0 MOLE;m1_m4:N12C[C@H](C(CC1)CC2)N2C(C1=CC=CC(=C1C=C2)CC)=O, amount is: 0.0 ;m0_m3:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4:CO, amount is: 0.0 ,Catalysts are m2_m5:[Pd], amount is: 0.0 MOLE.Products are 0:N12C[C@H](C(CC1)CC2)N2C(C1=CC=CC(=C1CC2)CC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (S)-2-(1-Azabicyclo[2.2.2]oct-3-yl)-5-ethyl-1(2H)-isoquinolinone (0.49 g, 1.5 mmol), from Example 2, was dissolved in methanol (10 ml) and reduced with hydrogen and 10% palladium on carbon at 50 psi for 5 hours. Filtration to remove the catalyst and evaporation of the methanol gave (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-5-ethyl-3,4-dihydro-1(2H)-isoquinolinone (0.48 g, 1.68 mmol), m.p. >290° C., [α]D25 -40.3° (c=0.64 H2O ). |
Here is a chemical reaction formula: Reactants are m1:N12C[C@H](C(CC1)CC2)N2C(C1=CC=CC(=C1C=C2)OC)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m0_m2:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:N12C[C@H](C(CC1)CC2)N2C(C1=CC=CC(=C1CC2)OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Proceeding as in Example 3, but replacing (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-5-ethyl-1(2H)-isoquinolinone with (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-5-methoxy-1(2H)-isoquinolinone, from Example 2, gave (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-3,4-dihydro-5-methoxy-1(2H)-isoquinolinone, m.p. >290° C. [α]D25 -45.7° (c=0.16 H2O). |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:BrBr, amount is: 0.0 MOLE;m1_m3_m2_m4:N12CC(C(CC1)CC2)N2C(C1=CC=CC=C1C=C2)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:C(C)(=O)O, amount is: 0.0 ;m1_m3_m2_m4:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N12CC(C(CC1)CC2)N2C(C1=CC=CC=C1C(=C2)Br)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of Br2 (1.0M) in glacial acetic acid (0.8 mL) was added to a solution of (RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-l(2H)-isoquinolinone (0.20 g; 0.787 mmol), from Example 2, in glacial acetic acid (5.0 mL). Thesolvent was removed under pressure and the residue was partitioned between methylene chloride (100 ml) and sodium carbonate (2.0M, 30 ml). The organic phase was separated and dried over anhydrous sodium sulfate. The mixture was then filtered and concentrated under reduced pressure. The solid residue was dissolved in ethyl alcohol (2 ml) and the solution acidified with hydrochloric acid (10%). A small amount of ethyl ether was added and crystals were collected and dried in vacuo to give (RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-4-bromo-1(2H)-isoquinolinone (0.0832 g, 0.248 mmol), m.p. 208°-209° C. |
Here is a chemical reaction formula: Reactants are m2:FC(C(=O)O)(F)F, amount is: 0.0 ;m3:[OH-].[Na+], amount is: 0.0 ;m1_m4:C(C)(C)(C)OC(=O)NCC(C(=O)OC)CC=C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C=C)C(CN)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve N-(t-butyloxycarbonyl)-2-(2-propenyl)-β-alanine, methyl ester(5.6 g, 23.0 mmol) in methylene chloride (25 mL) and treat with trifluoroacetic acid (15 mL). Stir for three hours and remove the volatiles in vacuo. Treat the residue with water, make basic with sodium hydroxide (1.0 g, 25 mmol) and extract with ethyl acetate. Separate the organic phase and dry (Na2SO4). Evaporate to give 4.0 g of the title compound as an oil in ethyl acetate. |
Here is a chemical reaction formula: Reactants are m2:ClC(C(OCC=C)=N)(Cl)Cl, amount is: 0.0 ;m3:FC(S(=O)(=O)O)(F)F, amount is: 0.0 ;m1_m4:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)N[C@@H](CO)C(=O)OC)CC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(Cl)Cl, amount is: 0.0 MOLE;m1_m4:C(Cl)Cl.C1CCCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)N[C@@H](COCC=C)C(=O)OC)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-L-serine, methyl ester (25 g, 63 mmol) in methylene chloride/cyclohexane (1:1, 600 mL). Add allyl trichloroacetimidate (26 g, 128 mmol) and trifluoromethanesulfonic acid (5 mL), 56.6 mmol). Stir at room temperatureunder a nitrogen atmosphere for 5 hours and dilute with methylene chloride.Wash with saturated aqueous sodium hydrogen carbonate , water, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (gradient 20% ethyl acetate/hexane to 35% ethyl acetate/hexane) to give the title compound; mp 95°-97° C. |
Here is a chemical reaction formula: Reactants are m2:CSC, amount is: 0.0 ;m1_m3:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)N[C@@H](COCC=C)C(=O)OC)CC1=CC=CC=C1, amount is: 0.0 ;m1_m3:C(Cl)Cl.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:O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)N[C@@H](COCC=O)C(=O)OC)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-O-2-propenyl-L-serine, methyl ester (13 g, 29.8 mmol) in methylene chloride/methanol (10:1, 220 mL). Cool to -78° C. and sparge with amixture of ozone/oxygen for approximately 10 minutes until a blue color persists. Sparge with nitrogen for 10 minutes at -78° C. to remove excess ozone. Treat with methylsulfide (60 mL, 0.82 mol) and allow to warmto room temperature. Stir at room temperature for 2.5 hours, evaporate the solvent in vacuo and dissolve the residue in ethyl acetate (200 mL). Wash with water, saturated sodium chloride, dry (MgSO4) and evaporate the solvent in vacuo to give the intermediate N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-O-2-oxoethyl-L-serine, methyl ester as a foam (13.6 g). |
Here is a chemical reaction formula: Reactants are m2:S(O)(O)(=O)=O, amount is: 0.0 ;m1_m3:C(C1=CC=CC=C1)OC(=O)N[C@@H](CN)C(=O)O, amount is: 0.0 ;m1_m3:CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)N[C@@H](CN)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve Nα -(benzyloxycarbonyl)-β-(amino)-L-alanine (47.6 g, 0.2 mol) in methanol (500 mL) and treat with concentrated sulfuric acid(0.5 mL). Heat to 60° C. for 16 hours, cool and reduce the solvent by 50% in vacuo. Dilute with ethyl ether (500 mL), wash with saturated sodium hydrogen carbonate, then brine. Dry (MgSO4) and evaporate the solvent in vacuo to give Nα -(benzyloxycarbonyl)-β-(amino)-L-alanine, methyl ester. |
Here is a chemical reaction formula: Reactants are m2:ClC(C(OCC=C)=N)(Cl)Cl, amount is: 0.0 ;m1_m4:C(C1=CC=CC=C1)OC(=O)N[C@@H](CN)C(=O)OC, amount is: 0.0 ;m3:FC(S(=O)(=O)O)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(Cl)Cl, amount is: 0.0 MOLE;m1_m4:C(Cl)Cl.C1CCCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)N[C@@H](CNCC=C)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve Nα -(benzyloxycarbonyl)-β-(amino)-L-alanine, methyl ester (15.9 g, 63 mmol) in methylene chloride/cyclohexane (1:1, 600mL). Add allyl trichloroacetimidate (26 g, 128 mmol) and trifluoromethanesulfonic acid (5 mL), 56.6 mmol). Stir at room temperatureunder a nitrogen atmosphere for 5 hours and dilute with methylene chloride.Wash with saturated aqueous sodium hydrogen carbonate, water, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give Nα -(benzyloxycarbonyl)-β-(allylamino)-L-alanine, methyl ester. |
Here is a chemical reaction formula: Reactants are m2:FC(C(=O)O)(F)F, amount is: 0.0 ;m1:B(Br)(Br)Br, 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(=O)[O-])(F)F.FC(C(=O)[O-])(F)F.FC(C(=O)[O-])(F)F.[B+3], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Place boron tribromide (215 mg, 0.86 mmol) in a flask and cool to 0°C. Cautiously add trifluoroacetic acid (5 mL) with stirring. Evaporate the solvent to give boron tris(trifluoroacetate). |
Here is a chemical reaction formula: Reactants are m1_m4:C1OC(C(=O)O)=C(C2=CC=CC=C2)O1, amount is: 0.0 ;m1_m4:C(C)(=O)O, amount is: 0.0 ;m3_m6:[Na], amount is: 0.0 MOLE;m2_m5:BrBr, amount is: 0.0 ;m2_m5:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m6:O, amount is: 0.0 ;m7:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1OC=2C=C(C=CC2O1)CC(C(=O)O)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Stir powdered methylenedioxy cinnamic acid (19.2 g, 210 mmol) in glacial acetic acid (200 mL) at room temperature while adding a solution of bromine (16 g, 100 mmol) in acetic acid (50 mL) over 30 minutes. Stir the homogeneous yellow solution for 15 minutes and add a solution of sodium cyabiborohydride (20 g) in water (50 mL) over 30 minutes. Stir for 48 hours at room temperature. Add water (70 mL) and stir for an additional 2 hours. Filter and wash the filtercake with acetic acid/water. Evaporate the solvent in vacuo and partition the residue between chloroform and water. Dry the organic phase (MgSO4) and evaporate the solvent in vacuo. Redissolve the residue in chloroform, filter and evaporate the solvent in vacuo to give 3-(3,4-methylenedioxyphenyl)-2-bromopropionic acid as a crystalline solid (15.1 g). |
Here is a chemical reaction formula: Reactants are m1_m2:N[C@H](CC1=CC=CC=C1)C(=O)O, amount is: 0.0 ;m1_m2:Br, amount is: 0.0 ;m3_m4:N(=O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C[C@H](C(=O)O)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix D-phenylalanine (186.4 g, 1.128 mol) and 49% hydrobromic acid (372.8 g), cool to -5° C. and add, by dropwise addition, a solution of sodium nitrite (77.9 g) in water (565 mL) over a period of about 1 hour (vigorous gas evolution). Stir at -5° C. to 0° C. for 4 hours, extract into ethyl ether (3×1L), dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (5% acetic aci/95% methylene chloride) and distillation to give 3-phenyl-2(R)-bromopropionic acid (112 g, 43%); bp 128°-135°C. @0.25 torr. |
Here is a chemical reaction formula: Reactants are m2_m4:ClC=1C=C(C(=O)OO)C=CC1, amount is: 0.0 ;m1_m3:BrC=1C=CC(=C(C=O)C1)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m4:C(Cl)(Cl)Cl, amount is: 0.0 ;m1_m3:C(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=CC(=C(C1)O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 5-bromo-2-methoxybenzaldehyde (100 g, 0.46 mol) in chloroform(250 ml) was cooled with an ice bath and 3-chloroperoxybenzoic acid (50-60%purity) (146 g, 0.51 mol) in chloroform (1000 ml) added. The reaction mixture was allowed to warm slowly to room temperature and stirred for 72 h. The white solid was filtered off and the filtrate concentrated in vacuo. The residue was dissolved in ether (200 ml) and washed with 1M sodium sulphite solution (2×200 ml) then sodium hydrogen carbonate [half saturated] (3×200 ml). The ether layer was washed with 10% aqueous sodium hydroxide (3×100 ml) and the combined basic extract was acidified with concentrated hydrochloric acid and extracted with Et2O (3×100 ml). The combined organic extract was dried (MgSO4) and florisil (10 g) filtered and the solvent removed under reduced pressure to give the title compound (90 g) as a pale brown solid. |
Here is a chemical reaction formula: Reactants are m1_m8:C1(CCCC1)OC1=C(C=CC(=C1)C1=CC(=CC=C1)[N+](=O)[O-])O, amount is: 0.0 ;m4:C1(=CC=CC=C1)O, amount is: 0.0 MOLE;m5_m6:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0 ;m5_m6:C1(CCCC1)Br, amount is: 0.0 ;m2_m3:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0 ;m2_m3:C1(CCCC1)Br, amount is: 0.0 ;m7:C1(=CC=CC=C1)O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m8:CN(C)C=O, amount is: 0.0 ;m9:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC1=C(C=CC(=C1)C1=CC(=CC=C1)[N+](=O)[O-])OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Cyclopentyloxy-4-(3-nitrophenyl)phenol (600 mg, 2.45 mmol) was dissolved in DMF (40 ml) and treated with Cs2CO3 (730 mg, 2.24 mmol) and cyclopentyl bromide (0.32 ml, 2.94 mmol). After stirring overnight at RT some of the phenol remained (SiO2 :t.l.c, CH2Cl2). Cs2CO3 (870 mg, 2.67 mmol) and cyclopentyl bromide (0.32 ml, 2.94 mmol) were added. After stirring at RT for 3 h the phenol had been consumed. The reaction mixture was filtered and concentrated in vacuo. The residue was dissolved in Et2O (50 ml), filtered, and concentrated in vacuo to give a yellow solid which was recrystallised fromdichloromethane/hexane to afford the title compound (378 mg) as yellow needles. δH (CDCl3 ; 80 mHz) 1.5-2.1 (8H, br m, (CH2)4), 3.87 (3H, s, OMe), 4.84 (1H, br m, OCHCH2), 6.91 (1 H, d, J9.1 Hz, ArH ortho to OMe), 7.0-7.2 (2H, m, ArH meta to OMe), 7.54 (1H, d, J7.5 Hz, ArH meta to NO2), 7.80 (1 H, ca. dt, Jca 7.5, 1.5 Hz, ArH para to NO2), 8.09 (1 H, ca. dt, J ca.8, 1.5 Hz, ArH parato aryl), 8.33 (1 H, ca. t, J ca 2 Hz, ArH ortho to NO2 and aryl); m/z313 (M+, 7%), 246 (17), 245 (M+ -cyclopentyl, 100), 230 (41), 202(8), and 139 (9). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C1(CCCC1)OC=1C=C(C=CC1OC)C=1C=NC=NC1, amount is: 0.0 ;m1_m2_m3:ClC=1C=C(C(=O)OO)C=CC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)C=1C=NC=[N+](C1)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 5-(3-Cyclopentyloxy-4-methoxyphenyl)pyrimidine (1.37 g) and 3-chloroperoxybenzoic acid (50.60%) (1.75 g) in dichloromethane (35 ml) was stirred at RT and the reaction followed by t.l.c. After 5 days, the reaction mixture was partitioned three times between dichloromethane (50 ml) and 10% aqueous Na2SO3 solution (50 ml). The combined organic phase was washed with 5% aqueous NaOH solution (3×30 ml), brine (30 ml), dried (MgSO4) and evaporated to afford a tan solid. Flash chromatography [SiO2 ; dichloromethane/EtOAc, 1:9 then dichloromethane/EtOAc/methane, 1:8:1] followed by recrystallisation from EtOAc furnished the title compound (390 g) as a white powder (mp 140°-143° C.). Found=C, 67.03; H, 6.31; N, 9.81. C16H18N2O3 requires C, 67.12; H, 6.34; N, 9.78%. |
Here is a chemical reaction formula: Reactants are m3:C(=O)(O)[O-].[Na+], amount is: 0.0 ;m1_m4_m2:[C-]#N.[K+], amount is: 0.0 ;m1_m4_m2:C1(CCCC1)OC=1C=C(C=CC1OC)C=1C=NC(=NC1)S(=O)(=O)C, 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:C1(CCCC1)OC=1C=C(C=CC1OC)C=1C=NC(=NC1)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of potassium cyanide (205 mg) in dry DMF (10 ml) was added the compound of Example 12 (1.0 g) and the reaction mixture stirred at room temperature for 3 hr then at 50° C. for 2 h. The reaction mixture was poured into a saturated NaHCO3 solution (2.5 g Na2CO3 in 120 ml ice). The resulting yellow precipitate was filtered offand washed with water. Recrystallisation from EtOAc/hexane (1:2) gave the title compound (575 mg) as yellow needles (mp 121°-123° C.).Found C, 69.15; H, 5.73; N, 14.13. C17H17N3O2 requires C, 69.14; H, 5.80; N, 14.23%. |
Here is a chemical reaction formula: Reactants are m1:ClC=1C(=NSN1)OC, amount is: 0.0 ;m2:S(=O)(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 ;m4:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C(=NSN1)OCCl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution comprised of 5 g of 60 percent pure 4-chloro-3-methoxy-1,2,5-thiadiazole in 30 mL of carbon tetrachloride was irradiated over a period of 45 minutes at 80° C. with a sunlamp while adding a solution comprised of 5 g of sulfuryl chloride in 20 mL of carbon tetrachloride. The reaction mixture was then washed with 30 mL of asaturated aqueous sodium bicarbonate solution and concentrated under reduced pressure to yield 4.87 grams of 4-chloro-3-chloromethoxy-1,2,5-thiadiazole. |
Here is a chemical reaction formula: Reactants are m1_m3:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=CC=C1)NC1=CC=CC=C1)=O, amount is: 0.0 ;m2:N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(CO)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 230 mg (0.7 mmol) of 4,5-bis(anilino)phthalic acid dimethylester in 23 ml of ethylene glycol is heated at 120°; ammonia gas is passed through the suspension, with stirring, for 24 hours. The reaction mixture is cooled and extracted with ethyl acetate. The ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed onsilica gel with dichloromethane/methanol 40:1 and the product fractions arecombined and concentrated by evaporation, yielding the title compound in the form of yellow crystals, m.p. 215°-217°, FAB-MS: 330 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC(=O)C#CC(=O)OC, amount is: 0.0 ;m1_m3_m2:C[Si](OC(=C)C(=C)O[Si](C)(C)C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C1=C(CC(=C(C1)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Under argon, a solution of 7.1 g (50 mmol) of acetylenedicarboxylic acid dimethyl ester in 30 ml of toluene is added dropwise to 12.5 g (50 mmol) of 2,3-bis(trimethylsilyloxy)-1,3-butadiene (95%) and then boiled under reflux for 19 hours. The reaction mixture is cooled, the solvent is evaporated off and the residue is distilled under a high vacuum (0.1 mbar,124°-127°), yielding the title compound in the form of a yellow, highly viscous oil, 1H-NMR (CDCl3): δ=0.18 (s, 18H), 3.09 (s, 4H), 3.78 (s, 6H). |
Here is a chemical reaction formula: Reactants are m1:COC(=O)C1=C(CC(=C(C1)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OC, amount is: 0.0 ;m2:NC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=CC=C1)NC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 5.6 g (15 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester and 5.5 ml (60 mmol) of aniline in 60 ml of glacial acetic acid is boiled under reflux for 4 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The crude product is recrystallized from ethanol, yielding the title compound in the form of yellow crystals, m.p. 178°, FAB-MS: 377 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m2:N(C1=CC=CC=C1)C=1C=C2C(C(=O)OC2=O)=CC1NC1=CC=CC=C1, amount is: 0.0 ;m1_m2:C(=O)N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 21.9 g (66.3 mmol) of 4,5-bis(anilino)phthalic anhydride in60 ml of formamide under argon atmosphere is heated at 125°-130° for 5 hours. The reaction mixture is cooled to 70°, and 250 ml of water are slowly added. This mixture is cooled to 0° for 30 minutes, and the reddish crystals are filtered off, washed with water and dried. Recrystallization from DMF/water yields the title compound in the form of orange crystals, m.p. 205°-207° C., FAB-MS: 330 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:N(C1=CC=CC=C1)C=1C=C(C(C(=O)O)=CC1NC1=CC=CC=C1)C(=O)O, amount is: 0.0 ;m1_m3_m2:C(C)(=O)OC(C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(C1=CC=CC=C1)C=1C=C2C(C(=O)OC2=O)=CC1NC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A steady stream of argon is passed through a suspension of 23.4 g (67.18 mmol) of 4,5-bis(anilino)phthalic acid in 250 ml of toluene, and 19.0 ml (201.5 mmol, 3 eq) of acetic anhydride is added. The reaction mixture is heated to 60°-65° for 90 minutes with vigorous stirring. Thereaction mixture is cooled to 10° for 30 minutes, and the yellow to orange crystals are filtered off and washed with toluene/hexane to yield the title compound in the form of yellow crystals, FAB-MS: 331 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m3:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=CC=C1)NC1=CC=CC=C1)=O, amount is: 0.0 ;m2_m4:O.[OH-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:CO, amount is: 0.0 ;m2_m4:O, amount is: 0.0 ;m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(C1=CC=CC=C1)C=1C=C(C(C(=O)O)=CC1NC1=CC=CC=C1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A steady stream of argon is passed through a suspension of 26.35 g (70.0 mmol) of 4,5-bis(anilino)phthalic acid dimethylester in 230 ml of methanol, and a solution of 11.78 g (280 mmol, 2 eq) of lithium hydroxide monohydrate in 116 ml of water is added. The reaction mixture is heated toreflux for 2.5 h, cooled to RT and diluted with 400 ml water. Methanol is removed by evaporation, the resulting solution is cooled to 0°, and70 ml 4N hydrochloric acid are added. After 15 min. at 0°, the gray crystals are filtered off, washed with water and resuspended twice in 200 ml toluene with removal of the toluene by distillation to yield the title compound in the form of gray crystals, FAB-MS: 349 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m3:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=C(C=C1)F)NC1=CC=C(C=C1)F)=O, amount is: 0.0 ;m2:N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(CO)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(NC=2C=C3C(C(=O)NC3=O)=CC2NC2=CC=C(C=C2)F)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Analogously to Example 1, 290 mg (0.7 mmol) of 4,5-bis(4-fluoroanilino)phthalic acid dimethyl ester in 22 ml of ethylene glycol are heated at 120° and, with stirring, ammonia gas is passedthrough the mixture for 18 hours. The reaction mixture is cooled and extracted with ethyl acetate. The ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel with hexane/ethyl acetate 1:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of orange crystals, m.p. >220° C., FAB-MS: 366 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m2:FC1=CC=C(N)C=C1, amount is: 0.0 ;m1:COC(=O)C1=C(CC(=C(C1)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=C(C=C1)F)NC1=CC=C(C=C1)F)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) and 2.3 ml (24 mmol) of 4-fluoroaniline in 60 ml of glacial acetic acid is boiled under reflux for 2 hours. The reactionmixture is cooled, the solvent is evaporated off and the dark-brown residueis dissolved in dichloromethane and the solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel with ethyl acetate/hexane 2:1 and the product fractions are concentrated by evaporation and recrystallized from ethyl acetate/hexane, yielding the title compound in the form of yellow crystals, 1H-NMR (CDCl3): δ=7.40 (s, 2H), 7.10-6.80 (m, 8H), 5.70 (br s2H), 3.83 (s, 6H). |
Here is a chemical reaction formula: Reactants are m1_m3:FC1=CC=C(NC=2C=C3C(C(=O)OC3=O)=CC2NC2=CC=C(C=C2)F)C=C1, amount is: 0.0 ;m1_m3:C(=O)N, amount is: 0.0 ;m2: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:FC1=CC=C(NC=2C=C3C(C(=O)NC3=O)=CC2NC2=CC=C(C=C2)F)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 1000 mg (2.73 mmol) of 4,5-bis(4-fluoroanilino)phthalic anhydride in 5 ml of formamide under argon atmosphere is heated at 125°-130° for 5 hours. The reaction mixture is cooled to 60°, and 20 ml of water are slowly added. This mixture is cooled to0° for 3 hours, and the reddish crystals are filtered off, washed with water and dried. Recrystallization from dichloromethane yields the title compound in the form of orange crystals, m.p. 244°-246° C., FAB-MS: 366 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:FC1=CC=C(NC=2C=C(C(C(=O)O)=CC2NC2=CC=C(C=C2)F)C(=O)O)C=C1, amount is: 0.0 ;m1_m3_m2:C(C)(=O)OC(C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(NC=2C=C3C(C(=O)OC3=O)=CC2NC2=CC=C(C=C2)F)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A steady stream of argon is passed through a suspension of 4.49 g (11.68 mmol) of 4,5-bis(4-fluoroanilino)phthalic acid in 75 ml of toluene and 3.32 ml (35.12 mmol, 3 eq) of acetic anhydride is added. The reaction mixture is heated to 60°-65° for 90 minutes with vigorous stirring. The reaction mixture is cooled to 10° for 15 minutes, theyellow orange crystals are filtered off and washed with toluene/hexane to yield the title compound in the form of yellow orange crystals, FAB-MS: 367 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m3:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=C(C=C1)F)NC1=CC=C(C=C1)F)=O, amount is: 0.0 ;m2_m4:O.[OH-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:CO, amount is: 0.0 ;m5:O, amount is: 0.0 ;m2_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(NC=2C=C(C(C(=O)O)=CC2NC2=CC=C(C=C2)F)C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A steady stream of argon is passed through a suspension of 5.0 g (12.12 mmol) of 4,5-bis(4-fluoroanilino)phthalic acid dimethylester in 40 ml of methanol, and a solution of 2.04 g (48.6 mmol, 2 eq) of lithium hydroxide monohydrate in 20 ml of water is added. The reaction mixture is heated to reflux for 1 hour, cooled to RT and diluted with 50 ml water. Methanol is removed by evaporation, the resulting solution is cooled to 0°, and12 ml 4N hydrochloric acid and thereafter 100 ml of water are added. After 15 min at 0°, the gray crystals are filtered off, washed with waterand resuspended twice in 100 ml toluene with removal of the toluene by distillation to yield the title compound in the form of gray crystals, FAB-MS: 385 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m3:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=C(C=C1)OCC1=CC=CC=C1)NC1=CC=C(C=C1)OCC1=CC=CC=C1)=O, amount is: 0.0 ;m2:N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(CO)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=CC=C(NC=2C=C3C(C(=O)NC3=O)=CC2NC2=CC=C(C=C2)OCC2=CC=CC=C2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Analogously to Example 1, 294.4 mg (0.5 mmol) of 4,5-bis(4-benzyloxy-anilino)phthalic acid dimethyl ester in 22 ml of ethylene glycol are heated at 120°, ammonia gas being passed through the mixture, with stirring, for 16 hours. The reaction mixture is cooled and extracted with ethyl acetate. The ethyl acetate phases are washed in succession three times with water and once with saturated sodiumchloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel withdichloromethane/methanol 50:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of red crystals, m.p. 187°-189° C., FAB-MS: 542 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)OC1=CC=C(N)C=C1, amount is: 0.0 ;m1:COC(=O)C1=C(CC(=C(C1)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=C(C=C1)OCC1=CC=CC=C1)NC1=CC=C(C=C1)OCC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) and 4.8 g (24 mmol) of 4-benzyloxyaniline in 24 ml of glacial acetic acid is boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is dissolved while hot in ethyl acetate and filtered, then allowed to crystallize at 0°. The crystalline residue is chromatographed on silica gel with ethyl acetate/hexane 3:2 and the product fractions are concentrated by evaporation and recrystallized from ethyl acetate/hexane, yielding the title compound in the form of beige crystals, FAB-MS: 589 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1:COC(=O)C1=C(CC(=C(C1)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OC, amount is: 0.0 ;m2:C(C)N(CC)C1=CC=C(N)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=C(C=C1)N(CC)CC)NC1=CC=C(C=C1)N(CC)CC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) and 3.94 g (24 mmol) of 4-(N,N-diethyl-amino)-aniline in 24 ml of glacial acetic acid is boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed onsilica gel with dichloromethane/methanol 400:15 and the product fractions are concentrated by evaporation and again chromatographed on silica gel with ethyl acetate/hexane 1:1. The product fractions are concentrated by evaporation, yielding the title compound in the form of green crystals, FAB-MS: 518 [M+ ], 519 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m4:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1CCCCC1)NC1CCCCC1)=O, amount is: 0.0 ;m2:N, amount is: 0.0 MOLE;m3:[Cl-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4:C(CO)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCCC1)NC=1C=C2C(C(=O)NC2=O)=CC1NC1CCCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Analogously to Example 1, 194 mg (0.5 mmol) of 4,5-bis(cyclohexylamino)phthalic acid dimethyl ester in 15 ml of ethylene glycol are heated at 120°, ammonia gas being passed through the mixture, with stirring, for 12 hours. The reaction mixture is cooled, saturated with sodium chloride and extracted with ethyl acetate. The ethylacetate phases are washed in succession three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed onsilica gel with hexane/ethyl acetate 3:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of orange crystals, m.p. 170°-175° C., FAB-MS: 342 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1:COC(=O)C1=C(CC(=C(C1)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OC, amount is: 0.0 ;m2:C1(CCCCC1)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1CCCCC1)NC1CCCCC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) in 21.5 ml (188 mmol) of cyclohexylamine and 4.5 ml of glacial acetic acid is boiled under reflux for 3.5 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 100 ml of 2N HCl, 50 ml of saturated NaHCO3and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel with ethyl acetate/hexane 5:12 and the product fractions are concentrated by evaporation and again chromatographed with ethyl acetate/hexane 1:4, yielding the title compound in the form of a yellow oil, FAB-MS: 388 [M+ ]. |
Here is a chemical reaction formula: Reactants are m1_m4:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=C(C=C1)OC)NC1=CC=C(C=C1)OC)=O, amount is: 0.0 ;m2:N, amount is: 0.0 MOLE;m3:[Cl-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4:C(CO)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=CC=C(NC=2C=C3C(C(=O)NC3=O)=CC2NC2=CC=C(C=C2)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Analogously to Example 1, 393 mg (0.9 mmol) of 4,5-bis(4-methoxyanilino)phthalic acid dimethyl ester in 25 ml of ethyleneglycol are heated at 120°, ammonia gas being passed through the mixture, with stirring, for 18 hours. The reaction mixture is cooled, saturated with sodium chloride and extracted with ethyl acetate. The ethylacetate phases are washed in succession three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed onsilica gel with ethyl acetate/hexane 1:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of yellow crystals, m.p. 191°-193° C., FAB-MS: 390 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m2:COC1=CC=C(C=C1)N, amount is: 0.0 ;m1:COC(=O)C1=C(CC(=C(C1)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=C(C=C1)OC)NC1=CC=C(C=C1)OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) and 3.0 g (24 mmol) of 4-anisidine in 24 ml ofglacial acetic acid is boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel withethyl acetate/hexane 1:1 and the product fractions are concentrated by evaporation, yielding the title compound in the form of a yellow foam, FAB-MS: 437 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1:COC(=O)C1=C(CC(=C(C1)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OC, amount is: 0.0 ;m2:IC1=C(N)C=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=C(C=CC=C1)I)NC1=C(C=CC=C1)I)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) and 5.3 g (24 mmol) of 2-iodoaniline in 24 ml of glacial acetic acid is boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The residue obtained after concentration by evaporation is chromatographed on silica gel with ethyl acetate/hexane 2:1 and the product fractions are concentrated by evaporation, yielding the title compound in the form of a yellow foam: 1H-NMR (DMSO-d6): δ=7.91 (dxd, J1 =8, J2 =1, 2H), 7.39 (dxdxd, J1 =10, J2 =8, J3 =1, 2H), 7.32 (br s, 2H), 7.22-7.05 (m, 2H), 7.01 (s, 2H), 6.88 (txd, Jt =8, Jd =1, 2H), 3.73 (s, 6H). |
Here is a chemical reaction formula: Reactants are m1_m3:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=CC=C1)N(C1=CC=CC=C1)C)=O, amount is: 0.0 ;m2:N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(CO)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Analogously to Example 1, 160 mg (0.41 mmol) of 4-(N-methyl-N-phenylamino)-5-anilinophthalic acid dimethyl ester in 12 ml of ethylene glycol are heated at 120° and, with stirring, ammonia gas is passed through the mixture for 18 hours. The reaction mixture is cooled and extracted with ethyl acetate. The ethyl acetate phases are washed in succession three times with water and once with saturated sodiumchloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel withhexane/ethyl acetate 1:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of slightly yellow crystals, FAB-MS: 344 [M+ +H], 1H-NMR (CDCl3): 3.28 (s, 3H). |
Here is a chemical reaction formula: Reactants are m1_m3:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=CC=C1)NC1=CC=CC=C1)=O, amount is: 0.0 ;m2:CN, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(CO)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(C1=CC=CC=C1)C=1C=C2C(C(=O)N(C2=O)C)=CC1NC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Analogously to Example 1, 376 mg (1 mmol) of 4,5-bis(anilino)phthalic acid dimethyl ester in 33 ml of ethylene glycol are heated at 120° and, with stirring, methylamine is passed through the mixture for 18 hours. Thereaction mixture is cooled and extracted with ethyl acetate. The ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed onsilica gel with hexane/ethyl acetate 1:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of slightly yellow crystals, FAB-MS: 344 [M+ +H], m.p. 195°-196° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC, amount is: 0.0 ;m1_m2_m3:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(C1=CC=CC=C1)C=1C=C2C(C(=S)NC2=O)=CC1NC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 138 mg (0.36 mmol) of Lawesson reagent [=2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiaphosphetane] are added to a solution of 100 mg (0.3 mmol) of 4,5-bis-(anilino)phthalimide (Example 1) in 15 ml of dichloromethane and the mixture is boiled under reflux for 4 hours. The reaction mixture is concentrated by evaporation and chromatographed directly on silica gel with hexane/ethyl acetate 2:1. The product fractions are concentrated by evaporation, yielding the title compound in the form of yellow crystals, FAB-MS: 346 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=CC=C(C=C1)OC, amount is: 0.0 ;m1_m3_m2:B(Br)(Br)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=CC=C(C=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 359.4 mg (1 mmol) of 4-anilino-5-(4-methoxy-anilino)-phthalimide in 5 ml of chloroform, a solution of 186 μl (2 mmol) boron tribromide is added dropwise at -40° C. to -30° C. The reaction mixture is stirred for 5 hours at -30° C., and is then quenched with 5 ml of water. The reaction mixture is warmed up to room temperature, and the phases are separated. The organic phase is washed twice with water, dried over magnesium sulfate and concentrated by evaporation. Excluding light, the evaporation residue is chromatographed with ethylacetate/hexane 1:1 on a silica gel column that is cooled with ice-water (double jacket), the product fractions are combined and concentrated by evaporation. The title compound is obtained in the form of yellow crystals, FAB-MS: 346 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1:COC(=O)C1=C(CC(=C(C1)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OC, amount is: 0.0 ;m2:COC1=CC=C(C=C1)N, amount is: 0.0 ;m3:NC1=CC=CC=C1, amount is: 0.0 ;m4:C(C)(=O)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:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=CC=C(C=C1)OC)NC1=CC=C(C=C1)OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4.8 g (12 mmol) 4,5-Bis(trimethylsilyloxy)-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a), 2.6 g (24 mmol) p-anisidine and 2.2 ml (24 mmol) aniline in 48 ml of glacial acetic acid is boiled under reflux for 2hours. The reaction mixture is cooled, the solvent is evaporated and the dark-brown residue is dissolved in ethyl acetate and the solution is washed in succession with 40 ml of 1N HCl, 100 ml of saturated NaHCO3and twice with water, dried with magnesium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel withethyl acetate/hexane 1:3 and the product fractions are concentrated by evaporation. This way, in the first product fractions 4,5-bis-(4-methoxy-anilino)-phthalic acid dimethyl ester is obtained in the form of a yellow foam: FAB-MS: 437 [M+ +H]. The evaporation residue of the product fractions following thereafter is recrystallized, and 4-anilino-5-(4-methoxy-anilino)-phthalic acid dimethyl ester is obtained in the form of yellow crystals, m.p. 122°-4° C., FAB-MS: 407 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=C(C=C(C=C1)OC)OC, amount is: 0.0 ;m1_m3_m2:B(Br)(Br)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=C(C=C(C=C1)O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 100 mg (0.26 mmol) of 4-anilino-5-(2,4-dimethoxy-anilino)-phthalimide in 8 ml of chloroform, a solution of 120 μl (1.24 mmol) boron tribromide is added dropwise at RT. The reaction mixture is stirred for 5 hours at RT, is then quenched with 5 ml of water and the phases are separated. The water phase is extracted three times with ethyl acetate. The organic phases are combined and washed twice with water, dried over magnesium sulfate and concentratedby evaporation. Excluding light, the evaporation residue is chromatographedwith ethylacetate/hexane 2:1 on a silica gel column (precoated with 0.1 g of sodium ascorbate per g silica gel) that is cooled with ice-water (double jacket), the product fractions are combined and concentrated by evaporation. Recrystallization from ethyl acetate/dichloromethane/hexane yields the title compound in the form of yellow crystals, m.p. 155°C. (decomp.), FAB-MS: 362 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=C(C=C(C=C1)OC)OC)NC1=CC=CC=C1)=O, amount is: 0.0 ;m2_m3_m4_m5:CO, amount is: 0.0 ;m2_m3_m4_m5:O.[OH-].[Li+], amount is: 0.0 ;m2_m3_m4_m5:O=C1C(O)=C([O-])[C@H](O1)[C@@H](O)CO.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3_m4_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(C1=CC=CC=C1)C=1C=C(C(C(=O)O)=CC1NC1=C(C=C(C=C1)OC)OC)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A steady stream of argon is passed through a suspension of 479 mg (1.09 mmol) of 4-anilino-5-(2,4-dimethoxy-anilino)phthalic acid dimethylester in3.6 ml of methanol, and a solution of 205 mg (4.905 mmol, 4.5 eq) of lithium hydroxide monohydrate and 10 mg sodium ascorbate in 1.7 ml of water is added. The reaction mixture is heated to reflux for 4 hours, cooled to RT, and the methanol is removed by evaporation. The resulting mixture is poured onto 20 ml of 4N hydrochloric acid, the red suspension is filtered and the crystals are washed with washed with isopropanol/hexane 1:5 to yield the title compound in the form of red crystals, TLC (dichloromethane/methanol 7:3) Rf =0.33. |
Here is a chemical reaction formula: Reactants are m4_m10:C(C(C)(C)C)(=O)O, amount is: 0.0 ;m1_m2_m11:COC(=O)C1=C(CC(=C(C1)O[Si](C)(C)C)O[Si](C)(C)C)C(=O)OC, amount is: 0.0 ;m1_m2_m11:C(C(C)(C)C)(=O)O, amount is: 0.0 ;m3_m6:COC1=C(N)C=CC(=C1)OC, amount is: 0.0 ;m5_m8:NC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m10:C(C)O, amount is: 0.0 ;m9:O, amount is: 0.0 MOLE;m7:O, amount is: 0.0 MOLE;m1_m2_m11:CN(C)C=O, amount is: 0.0 ;m3_m6:CN(C)C=O, amount is: 0.0 ;m5_m8:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=C(C=C(C=C1)OC)OC)NC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.31 g (3 mmol) 4,5-Bis(trimethylsilyloxy)-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a), 306 mg (3 mmol) pivalic acid and 1 ml of DMF is heated under argon to 120° and a solution of 460 mg (3 mmol) 2,4-dimethoxy-anilin in 1 ml of DMF is added within 5 minutes. The reaction mixture is heated at 120° for 10 minutes, cooled, diluted with water and extracted with ethyl acetate. The organic phase is washed in succession with 1N HCl, water, saturated Na2CO3, water and brine, dried with magnesium sulfate and concentrated by evaporation. The evaporation residue, a brown oil, 402 mg (3.9 mmol) pivalic acid and 2 ml of ethanol are heated to reflux and a solution of 358 μl (3.9 mmol) of aniline in 3 ml of ethanol is added dropwise. The reaction mixture is heated to reflux for 15 hours, cooled, diluted with water and extracted with ethyl acetate. The organic phase is washed in succession with 1N HCl,water, saturated Na2CO3, water and brine, dried with magnesium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel with ethyl acetate/hexane 1:2 and the product fractions are concentrated by evaporation. This way, in the first product fractions 4-anilino-5-(2,4-dimethoxy-anilino)-phthalic acid dimethyl ester is obtained in the form of a yellow oil: FAB-MS: 437 [M+ +H]. The evaporation residue of the product fractions following thereafter is recrystallized, and 4,5-bis-(2,4-dimethoxy-anilino)-phthalicacid dimethyl ester is obtained in the form of a yellow foam: FAB-MS: 497 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m3_m4_m5:[Li], amount is: 0.0 ;m3_m4_m5:O=C1C(O)=C([O-])[C@H](O1)[C@@H](O)CO.[Na+], amount is: 0.0 ;m1_m2:COC(C=1C(C(=O)OC)=CC(=C(C1)NC1=C(C=C(C=C1)OC)OC)NC1=C(C=C(C=C1)OC)OC)=O, amount is: 0.0 ;m1_m2:CO, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m4_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=C(NC=2C=C(C(C(=O)O)=CC2NC2=C(C=C(C=C2)OC)OC)C(=O)O)C=CC(=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A steady stream of argon is passed through a suspension of 260 mg (0.6 mmol) of 4,5-bis(2,4-dimethoxy-anilino)phthalic acid dimethylester in 2 mlof methanol, and a solution of 101 mg (2.4 mmol, 4 eq) of lithium hydroxidemonohydrate and 10 mg sodium ascorbate in 1 ml of water is added. The reaction mixture is heated to reflux for 10 hours, cooled to RT, and the methanol is removed by evaporation. The resulting mixture is poured onto 20 ml of 4N hydrochloric acid, the red suspension is filtered and the crystals are washed with washed with isopropanol/hexane 1:5 to yield the title compound in the form of red crystals, FAB-MS: 469 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=CC(=C(C=C1)OC)OC, amount is: 0.0 ;m1_m3_m2_m4:B(Br)(Br)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:ClCCl, amount is: 0.0 ;m1_m3_m2_m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=CC(=C(C=C1)O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 219 mg (0.56 mmol) of 4-anilino-5-(3,4-dimethoxy-anilino)-phthalimide in 5 ml of dichloromethane, a solution of 270 μl (2.8 mmol) boron tribromide in 3 ml of dichloromethane is added dropwise at RT. The reaction mixture is stirred for 5 hours at RT and then quenched with 5 ml of water, and the phases are separated. The water phase is extracted three times with ethyl acetate. The organic phases are combined and washed twice with water, dried over magnesium sulfate and concentrated by evaporation. Excluding light, the evaporation residue is chromatographed with ethylacetate/hexane2:1 on a silica gel column (precoated with 0.1 g of sodium ascorbate per g silica gel) that is cooled with ice-water (double jacket), and the productfractions are combined and concentrated by evaporation. Recrystallization from ethyl acetate/dichloromethane/hexane yields the title compound in theform of orange crystals, FAB-MS: 362 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m2:B(Br)(Br)Br, amount is: 0.0 ;m1:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=CC(=C(C(=C1)OC)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:N(C1=CC=CC=C1)C=1C=C2C(C(=O)NC2=O)=CC1NC1=CC(=C(C(=C1)O)O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 78 mg (0.18 mmol) of 4-anilino-5-(3,4,5-trimethoxy-anilino)-phthalimide (Example 27) in 4 ml ofdichloromethane, a solution of 314 μl (3.24 mmol) boron tribromide is added dropwise at RT. The reaction mixture is stirred for 4 hours at RT, is then cooled to 0° and quenched with 5 ml of water, and the phases are separated. The water phase is extracted three times with ethyl acetate. The organic phases are combined and washed twice with water, dried over magnesium surf ate and concentrated by evaporation. Excluding light, the evaporation residue is chromatographed with ethylacetate/dichloromethane 4:1 on a silica gel column (precoated with 0.4 g of sodium ascorbate per g silica gel) that is cooled with ice-water (double jacket), the product fractions are combined and concentrated by evaporation yielding the title compound in the form of dark red crystals, m.p. 152° C. (decomp.), FAB-MS: 378 [M+ +H]. |
Here is a chemical reaction formula: Reactants are m2:C1(CC1)N, amount is: 0.0 ;m1:ClC=1C=C(C=CC1[N+](=O)[O-])C1CCC=2N1C=NC2, 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(CC1)NC1=C(C=CC(=C1)C1CCC=2N1C=NC2)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3.15 g of 5-(3-chloro-4-nitrophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol (preparedas described in EP-A-0,426,225) and 30 ml of cyclopropanamine was stirred for 30 hours at reflux temperature. The reaction mixture was evaporated and the residue was stirred in water. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was co-evaporated with methylbenzene, yielding 3.4 g (99.6%) of (±)-N-cyclopropyl-5-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-2-nitrobenzenamine (interm. 6). |
Here is a chemical reaction formula: Reactants are m1:COC1=CC=C2C3=C(NC2=C1)CCCCC3C, amount is: 0.0 ;m4_m5:[Cl-].[Al+3].[Cl-].[Cl-], amount is: 0.0 MOLE;m4_m5:C(C)S, amount is: 0.0 MOLE;m6:Cl, amount is: 0.0 MOLE;m2_m3:[Cl-].[Al+3].[Cl-].[Cl-], amount is: 0.0 ;m2_m3:C(C)S, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)SC1=CC=C2C3=C(NC2=C1)CCCCC3C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 500 mg (1.9 mmol) of the compound obtained in Stage B of Example 1, predissolved in 5 cm3 of methylene chloride distilled over phosphoruspentoxide are added dropwise to a mixture, cooled to 0° C., of 380 mg (2.84 mmol) of aluminum chloride and 2.3 g (37.9 mmol) of ethanethiol. After stirring for 1 h at 0° C., 1.5 eq. of aluminum chloride and 20 eq. of ethanethiol are added again. The mixture is stirred again for 1 h at 0° C. and then poured onto ice, treated with 1N hydrochloric acid and then extracted with dichloromethane. After treatment of the organic phase and purification of the crude product by chromatography on asilica column, the expected compound is obtained. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C)(C)(C)C=1C=C(C(=O)N)C=C(C1O)C(C)(C)C, amount is: 0.0 ;m1_m2_m3_m4:COC(CC(C(C)Br)=O)=O, amount is: 0.0 ;m1_m2_m3_m4:O1CCOCC1, amount is: 0.0 ;m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC(CC=1N=C(OC1C)C1=CC(=C(C(=C1)C(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 mixture of 3,5-di-tert-butyl-4-hydroxybenzamide (16.0 g, 64.3 mmol), 4-bromo-3-oxopentanoic acid methyl ester (18.6 g, 64.26 mmol), dioxane (60mL), and toluene (600 mL) was refluxed for 5 days with continuous water removal (Dean Stark trap). Then, the volatiles were removed in vacuo and the residue was purified by flash chromatography on silica gel (eluting solvent: hexane/EtOAc 3/1) to give a brown viscous oil (11.2 g). Crystallization of the brown oil from ethyl ether (after cooling to 0° C.) gave a white solid (9.2 g, 40% yield), m.p. 121°-123° C. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 MOLE;m1_m2_m3_m6:[OH-].[Na+], amount is: 0.0 ;m1_m2_m3_m6:COC(CC=1N=C(OC1C)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)=O, amount is: 0.0 ;m1_m2_m3_m6:CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE;m1_m2_m3_m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=1OC(=C(N1)CC(=O)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium hydroxide (2N, 5.0 mL, 10.0 mmol) was added to a solution of [2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyloxazol-4-yl]-acetic acid methyl ester (1.5 g, 4.18 mmol), MeOH (15 mL), and THF (15 mL). After stirring for 1 hour, the mixture was poured into water, acidified with HCl(2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from acetone/ethyl ether/hexane gave a white solid (1.25 g, 87% yield), m.p. 205°-206° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=1OC(=C(N1)CC(=O)O)C, amount is: 0.0 ;m1_m2_m3:CCO, amount is: 0.0 ;m1_m2_m3:S(O)(O)(=O)=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(C)OC(CC=1N=C(OC1C)C1=CC(=C(C(=C1)C(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 mixture of [2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyloxazol-4-yl]-acetic acid (1.5 g, 4.35 mmol), EtOH (50 mL), and concentrated sulfuric acid (0.5 mL) was refluxed for 10 hours. The mixture poured into water, and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from ethyl ether/hexane gave a light brown solid (1.35g, 83% yield), m.p. 103°-105° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C)(C)(C)C=1C=C(C(=O)N)C=C(C1O)C(C)(C)C, amount is: 0.0 ;m1_m2_m3_m4:ClCC(CC(=O)OC)=O, amount is: 0.0 ;m1_m2_m3_m4:O1CCOCC1, amount is: 0.0 ;m1_m2_m3_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC(CC=1N=C(OC1)C1=CC(=C(C(=C1)C(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 mixture of 3,5-di-tert-butyl-4-hydroxybenzamide (5.0 g, 20.0 mmol), methyl 4-chloroacetoacetate (3.01 g, 20.0 mmol), dioxane (30 mL), and toluene (300 mL) was refluxed for 5 days, with continuous water removal (Dean Stark trap). The volatiles were removed in vacuo and the residue waspurified by flash chromatography on silica gel (eluting solvent: hexane/EtOAc 3/1) to give a brown viscous oil (3.2 g). Crystallization of the brown oil from ethyl ether (after cooling to 0° C.) gave a white solid (2.6 g, 38% yield), m.p. 126°-128° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=1OC(=C(N1)CC(=O)O)C, amount is: 0.0 ;m1_m2:CON=C=NC(C)(C)C, amount is: 0.0 ;m3:C1CCOC1, amount is: 0.0 ;m4_m0:CCCCCC.CCOC(=O)C, 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:COC(NC(CC=1N=C(OC1C)C1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of [2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyloxazol-4-yl]-acetic acid (2.0 g, 5.8 mmol), N-methoxy-N'-tert-butylcarbodiimide (0.9 g, 5.8 mmol) prepared according to Bull. Chem. Soc. Japan 45, 3607-3611 (1972) and THF (20 mL) was refluxed for 6 hours. The volatiles were removed in vacuo, andthe residue was purified by flash chromatography on acid washed silica gel (5% H3PO4 in MeOH), eluting solvent: hexane/EtOAc 3/1, to give an off-white solid (2.2 g, 94% yield), m.p. 125°-127° C. |
Here is a chemical reaction formula: Reactants are m4:ClC(=O)OC, amount is: 0.0 ;m3_m7:FC(C1=CC=C(C=C1)NC(=O)N1N=C2C3=C(CCC2C1)C=CC=C3)(F)F, amount is: 0.0 ;m1_m5_m2_m6:C(C)(C)NC(C)C, amount is: 0.0 ;m1_m5_m2_m6:C(CCC)[Li], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m7:C1CCOC1, amount is: 0.0 ;m1_m5_m2_m6:C1CCOC1, amount is: 0.0 ;m1_m5_m2_m6:CCCCCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC(=O)C12CN(N=C2C2=C(CC1)C=CC=C2)C(=O)NC2=CC=C(C=C2)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 0.9 ml of diisopropylamine in 10 ml of THF, at -78°C., was added 2.3 ml of 2.5 M n-butyl lithium in hexane and the mixture wasstirred for 5 mins. To this solution was added a solution of 1.0 g of the title compound of Step A in 5 ml of THF. The reaction was warmed to 0° C., recooled to -78° C. and then 0.75 ml of methyl chloroformate was added. The reaction mixture was then stirred for 24 h, with gradual warming to room temperature, quenched with 0.5 ml of glacial acetic acid, and poured into a 5% solution of aqueous NaHCO3. The mixture was extracted with chloroform, dried over magnesium sulfate and concentrated. Chromatography on silica gel with 30% ethyl acetate hexane afforded 0.25 g of the title compound, m.p. 177° to 180° C. |
Here is a chemical reaction formula: Reactants are m3:S(Cl)Cl, amount is: 0.0 ;m1_m2:CC(C)NC(OCC)=O, amount is: 0.0 ;m1_m2:[Cl-], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:N1=CC=CC=C1, amount is: 0.0 MOLE;m5:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClSN(C(OCC)=O)C(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of ethyl (1-methylethyl)carbamate (13.1 g, 0.1 mol) in 100 mlmethylene chloride cooled to 0° C. was added sulfur dichloride (11.3g, 0.11 mol) in one portion. While maintaining the temperature of the mixture at 0° C., pyridine (8.7 g, 0.11 mol) was added dropwise over eleven minutes. After complete addition of the pyridine the temperature was allowed to rise to room temperature and stirring was continued for additional 1.5 hours. The mixture was let stand overnight. Methylene chloride was evaporated under vacuum and 100 ml hexane was added. Filteration of the pyridine hydrochloride and evaporation of hexaneresulted in an orange oil which was distilled in a Kugelrohr apparatus to give 12.5 g of the title compound Bp: 64°-80° (bath temperature) at 1.4 mm Hg. |
Here is a chemical reaction formula: Reactants are m2_m3:C(C)N(CC)CC, amount is: 0.0 ;m2_m3:ClSN(C(OCC)=O)C(C)C, amount is: 0.0 ;m1_m4_m5:COC(=O)C12CN(N=C2C2=C(CC1)C=CC=C2)C(=O)NC2=CC=C(C=C2)C(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC(=O)C12CN(N=C2C2=C(CC1)C=CC=C2)C(=O)N(SN(C(=O)OCC)C(C)C)C2=CC=C(C=C2)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the title compound of Step B (2.0 g, 4.8 mmol) in 5 0 ml methylene chloride cooled to 0° C. was added triethylamine (1.0 g, 0.01 mol) and ethyl (chlorosulfenyl) (1-methylethyl)carbamate from Step D (1.4 g, 7.7 mmol). The mixture was allowed to warm to room temperature andstirred for one hour. The crude mixture was purified by silica column chromatography using ether-hexane (1:2) as eluent. The title compound (2.38 g) was obtained in about 90% purity (mp: 130°-134° ). Extraction of the product with ether-hexane (2:1) gave 1.8 g of highly pure material mp: 139°-140° C. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC(=O)SCl, amount is: 0.0 ;m1_m2:CC(CC)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:CC(CC)OC(=O)SCl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Chlorocarbonylsulfenyl chloride (13.1 g, 0.1 mol) was mixed with 2-butanol (6.7 g, 0.09 mol) and warmed to about 35° to 40° C. for one hour. Distillation resulted in the title compound (5.93 g) Bp. 70° C./0.8 mm Hg. NMR spectrum was consistent with the structure. |
Here is a chemical reaction formula: Reactants are m1_m6_m2:COC(=O)C12CN(N=C2C2=C(CC1)C=CC=C2)C(=O)NC2=CC=C(C=C2)C(F)(F)F, amount is: 0.0 ;m1_m6_m2:C(C)N(CC)CC, amount is: 0.0 ;m3:CC(CC)OC(=O)SCl, amount is: 0.0 ;m4_m5:CC(CC)OC(=O)SCl, amount is: 0.0 ;m4_m5:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C12CN(N=C2C2=C(CC1)C=CC=C2)C(=O)N(SC(=O)OC(CC)C)C2=CC=C(C=C2)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the title compound of Step B (Example 1) 0.4 g, 0.96 mmol)in 5 ml methylene chloride was added triethylamine (0.12 g) and cooled to 0° C. To this solution was added (1-methylpropoxycarbonyl)sulfenyl chloride (Step A) (0.2 g, 0.0012 mol). The mixture was stirred at room temperature for one hour. At this stage thin layer chromatography indicated only partial conversion, therefor, additional amounts of (1-methylpropoxycarbonyl)sulfenyl chloride (0.2 g) and triethylamine (0.12g) was added and the mixture was let stand over night. The reaction mixturewas subjected to silica gel column chromatography using hexane-ether (7:1) as eluent. The title compound was obtained (0 g) in high purity; m.p.: 125°-126° C. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC=1C=CC2=C(CCC3(CN(N=C23)C(=O)NC2=CC=C(C=C2)C(F)(F)F)C(=O)OC)C1, amount is: 0.0 MOLE;m1_m2:C(Cl)Cl, amount is: 0.0 MOLE;m4_m3:ClSN(C(OCCCCCC)=O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4_m3:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=CC2=C(CCC3(CN(N=C23)C(=O)N(SN(C(=O)OCCCCCC)C)C2=CC=C(C=C2)C(F)(F)F)C(=O)OC)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of the title compound of Step E above (2.2 g, 0.005 mol) in25 ml methylene chloride cooled to 0° C. was added triethylamine (1.0 g) and hexyl (chlorosulfenyl)(methyl)carbamate, (prepared in a mannersimilar to Example 1, Step D), (2.5 g 75% pure) dropwise at 0° C. The mixture was stirred at room temperature for additional one hour. The reaction mixture was concentrated under high vacuum and subjected to silica gel column chromatography using hexane-ether (1:1) as an eluent. The title compound (2.5 g) was obtained, melting point 128°-129° C. in high purity. |
Here is a chemical reaction formula: Reactants are m3:S(Cl)Cl, amount is: 0.0 ;m1_m2:CC(C)NC(OCC)=O, amount is: 0.0 ;m1_m2:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:N1=CC=CC=C1, amount is: 0.0 ;m4:N1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClSN(C(OCC)=O)C(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of ethyl (1-methylethyl)carbamate (13.1 g, 0.1 mol) in 100 mlof methylene chloride cooled to 0° C. was added sulfur dichloride (11.3 g, 0.11 mol) in one portion. While maintaining the temperature of the mixture at 0° C., pyridine (8.7 g, 0.11 mol) was added dropwiseover eleven minutes. After complete addition of the pyridine the temperature was allowed to rise to room temperature and stirring was continued for additional 1.5 hours. The mixture was let stand overnight. Methylene chloride was evaporated under vacuum and 100 ml hexane was added. Filteration of pyridine in hydrochloride and evaporation of hexane resulted an orange oil which was distilled in a Kugelrohr apparatus to give 12.5 g of the title Compound B.P.: 64°-80° (bath temp.) |
Here is a chemical reaction formula: Reactants are m1_m4:COC([C@H]1N(CCC1)C[C@H](CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)NC(=O)OC(C)(C)C)=O, amount is: 0.0 ;m3:Cl, amount is: 0.0 ;m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)N[C@H](CN1[C@H](C(=O)O)CCC1)CSC(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: [2(R)-(t-butyloxycarbonyl)amino-3-triphenylmethylmercaptopropyl]-L-proline methyl ester (0.325 g, 0.58 mmol) was dissolved in MeOH (12 mL) and 1N NaOH solution (2.3 mL, 2.3 mmol) with stirring at ambient temperature. After 24 hrs, the reaction mixture was concentrated to remove MeOH, then dissolved in H2O, neutralized with 1N HCl (2.3 mL, 2.3 mmol), and extracted with EtOAc (3×10 mL). The organics were combined, washed with brine and dried (Na2SO4). Filtration and concentration to dryness provided the title compound. 1H NMR (CD3OD) δ 7.2-7.5 (m, 15H), 3.7-3.85 (m, 1H), 3.5-3.7 (m, 2H), 2.9-3.15 (m, 3H), 2.2-2.6 (m, 3H), 1.8-2.2 (m, 3H), 1.48 (s, 9H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m6:C(C)(C)(C)OC(=O)N[C@H](CN1[C@H](C(=O)O)CCC1)CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m6:CN(CCCN=C=NCC)C, amount is: 0.0 ;m1_m2_m3_m6:O.ON1N=NC2=C1C=CC=C2, amount is: 0.0 ;m5:CCN(CC)CC, amount is: 0.0 ;m4:ClC1=C(CN)C=CC=C1Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m6:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)N[C@H](CN1[C@H](C(=O)O)CCC1)CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.ClC1=C(C(=O)N)C=CC=C1Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: [2(R)-(t-butoxycarbonyl)amino-3-triphenylmethylmercaptopropyl]-L-proline (0.08 g, 0.153 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC) (0.035 g, 0.184 mmol), and 1-hydroxybenzotriazole hydrate (HOBT) (0.025 g,0.184 mmol) were dissolved in DMF (2 mL), treated with 2,3-dichlorobenzylamine (0.025 mL, 0.184 mmol), and brought to pH 7 with Et3N (0.026 mL, 0.184 mmol). After stirring at ambient temperature for 18 h the mixture was concentrated to dryness, and the residue was partitioned between EtOAc and H2O, the organic layer separated, washed with aq satd NaHCO3, brine, and dried (Na2SO4). Filtration and concentration provided the title compound. 1H NMR (CD3OD) δ 7.1-7.5 (m, 18H), 4.53 (d, 1H, J=8 Hz), 4.26 (d, 1H,J=8 Hz), 3.64-3.76 (m, 1H), 2.96-3.14 (m, 2H), 2.52-2.66 (m, 1H), 2.1-2.5 (m, 5H), 1.6-1.9 (m, 3H), 1.45 (s, 9H). |
Here is a chemical reaction formula: Reactants are m2_m3:C(F)(F)(F)C(=O)O, amount is: 0.0 ;m2_m3:C(C)[SiH](CC)CC, amount is: 0.0 ;m1_m4:CC1=C(C=CC=C1C)NC([C@H]1N(CCC1)C[C@H](CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)NC(=O)OC(C)(C)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C=CC=C1C)NC([C@H]1N(CCC1)C[C@H](CS)N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-[2(R)-t-butoxycarbonylamino-3-triphenylmethylmercapto-propyl]-L-proline-2,3-dimethylphenyl amide (0.124 g, 0.19 mmol) was dissolved in CH2Cl2 (3 mL) and CF3CO2H (1 mL) at ambient temperature, treated with triethylsilane (0.121 mL, 0.76 mmol) and stirred for 2 h. Thereaction mixture was concentrated, triturated with 0.1% aq TFA soln, the solid precipitate filtered off, and the filtrate lyophilized to provide the title compound. 1H NMR (CD3OD) δ 7.10 (s, 3H), 3.55-3.68 (m, 1H), 3.32-3.45 (m, 2H), 2.75-3.19 (m, 5H), 2.5-2.65 (m, 1H),2.31 (s, 3H), 2.15 (s, 3H), 1.9-2.15 (m, 3H). |
Here is a chemical reaction formula: Reactants are m2:C(C)N(CC)CC, amount is: 0.0 ;m3_m5:C(C)(C)(C)N, amount is: 0.0 ;m1_m4:C=1(C(=CC=CC1)C(=O)Cl)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:C(Cl)Cl, amount is: 0.0 ;m6:O, amount is: 0.0 ;m1_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)NC(C1=C(C=CC=C1)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a cold (0° C.) solution of 139.2 g (0.9 mol) of o-toluoyl chloride in 1200 mL of methylene chloride at 25° C., under nitrogen, was slowly added 180.0 g (1.8 mol) of triethylamine followed by the dropwise addition of a solution containing 73.14 g (1.0 mol) of t-butylamine in 200 mL of methylene chloride. The resulting reaction mixture was warmed to room temperature and allowed to react for 2.5 hours.The reaction mixture was then diluted with 1800 mL of water. The resulting layers were separated, and the organic layer was washed sequentially with 2N sodium hydroxide, 1.0N hydrochloric acid and brine, dried over magnesium sulfate, filtered and then reduced to dryness under reduced pressure to provide 167.6 g of an off-white solid |
Here is a chemical reaction formula: Reactants are m1:C(=O)(O)C1NCC2=CC=CC=C2C1, amount is: 0.0 ;m2:C=O, amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:C(=O)O, amount is: 0.0 ;m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN1CC2=CC=CC=C2CC1C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.364 g (2.07 mmol) of 3-carboxy-1,2,3,4-tetrahydroisoquinoline in 25 mL of formic acid was combined with 2.5 mL of 37% formaldehyde. The resulting mixture was allowed to reflux for approximately 17 hours. After cooling, the mixture was contentrated under reduced pressure to provide a gum. This gum was dissolved in 3.0 mL of water, adjusted to a pH 2 using hydrochloric acid and then purified using ion-exchange chromatography (Dowex 50x-8, 100 meshcation) to provide 0.21 g of a yellow powder. |
Here is a chemical reaction formula: Reactants are m1_m2:S(=O)(=O)(O)CC(=O)O, amount is: 0.0 ;m1_m2:CCO, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:S(=O)(=O)(O)CC(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sulfoacetic acid (52 g, 371 mM) and EtOH (500 mL) were heated under reflux for 20 hours. The reaction mixture was cooled, and the excess ethanol was removed under vacuum to give ethyl sulfoacetate. |
Here is a chemical reaction formula: Reactants are m1_m2:S(=O)(=O)(O)CC(=O)OCC, amount is: 0.0 ;m1_m2:O=P(Cl)(Cl)Cl, 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:ClS(=O)(=O)CC(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1H NMR (CDCl3):δ1.35 (t, 3H), 4.1 (s, 2H), 4.25 (q, 2H). Amixture of ethyl sulfoacetate (16.82 g, 100 mM) and POCl3 (30.67 g, 200 mM) was heated at 125° C. for 5 hours. The mixture was cooled and filtered, and excess POCl3 was removed to give ethyl chlorosulfonylacetate. The ethyl chlorosulfonylacetate (8.18 g, 43.83 mM) was added dropwise with stirring to a solution of 2,6-diisopropylaniline (15.54 g, 87.66 mM) in 50 mL CH2Cl2 maintained at 0° C. The mixture was stirred at room temperature for an additional 18 hours. The solvent was removed and the residue was redissolved in 100 mL ethyl acetate and washed with 1N HCl and brine. The ethyl acetate was evaporatedand the pure compound was isolated by chromatography over silica gel (EtOAc/hexane, 1:4 as eluant) as a white powder identified as ethyl (2,6-diisopropylphenylsulfamoyl)acetate, 7.0 g (≈50%), mp 74°-77° C. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m1_m2_m3_m5:ClCC(=O)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m5:SCC(=O)OCC, amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m5:O1CCCC1, 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(C(=O)C1=CC=CC=C1)CC(=S)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Part A. A solution of 2-chloroacetophenone (Aldrich, 14.1 g, 91.2 mmol), ethyl 2-mercaptoacetate (Aldrich, 10.0 mL, 91.2 mmol), and potassium carbonate (13.9 g, 100 mmol) in tetrahydrofuran (200 mL) was stirred at ambient temperature for 10 hours. The mixture was poured into water (400 mL), and extracted with methylene chloride (2×400 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane) to afford the product, ethyl 2-phenacylthioacetate, as an oil (16.1 g, 67.7 mmol, 74%). 1H NMR (CDCl3): δ 7.97 (2H, dd, J=8.0, 1.5 Hz); 7.62 (1H, tt, J=5.1, 1.4 Hz); 7.48 (2H, t, J=7.7 Hz); 4.19 (2H, q, J=7.3 Hz); 4.04 (2H, s); 3.33 (2H, s); 1.27 (3H, t, J=7.3 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 256 (100%); 240 (6%);239 (42%); 210 (1%); 193 (1%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(CCCC)C1C(SC(C=C1)CCCCC)C(=O)OCC, amount is: 0.0 MOLE;m1_m2_m3:[OH-].[Na+], amount is: 0.0 MOLE;m1_m2_m3:C(C)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:C(CCCC)C1C(SC(C=C1)CCCCC)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Part C. A solution of the ester compound from Part B above (4.53 g, 14.5 mmol) and sodium hydroxide (0.25N solution) in 95% ethanol (120 mL, 30.0 mmol NaOH) was stirred for 12 hours at ambient temperature. The reaction mixture was evaporated, and the residue acidified with hydrochloric acid (1N, 150 mL). This was saturated with sodium chloride and extracted with methylene chloride (2×200 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the product, 3,6-dipentyl-3,6-dihydro-2H-thiopyran-2-carboxylic acid, as an oily mixture of diastereomeric products (5:1 by NMR) (4.01 g, 14.1 mmol, 97%). 1H NMR (major isomer; CDCl3): δ 5.73 (2H, s); 3.48 (1H, br t, J=7 Hz); 3.40 (1H, d, J=3.7 Hz); 2.60-2.52 (1H, m); 1.71-1.24 (16H, m); 0.89 (6H, t, J=3.7 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 287 (6%); 286 (18%); 285 (100%); 239 (25%); 211 (2%). |
Here is a chemical reaction formula: Reactants are m1_m2_m5:NC=1C(=NC(=CC1SC)C)SC, amount is: 0.0 ;m1_m2_m5:C(C)N(CC)CC, amount is: 0.0 ;m3_m6:ClCC(=O)Cl, amount is: 0.0 ;m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:O1CCCC1, amount is: 0.0 ;m3_m6:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CSC1=NC(=CC(=C1NC(CCl)=O)SC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Part A. A solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (0.38 g,1.88 mmol) and triethylamine (0.30 mL, 2.07 mmol) in tetrahydrofuran (8 mL)was cooled to 0° C., and treated with a solution of chloroacetyl chloride (0.18 mL, 2.26 mmol) in tetrahydrofuran (4 mL). After being stirred for 10 hours, the mixture was poured into water (100 mL), and thiswas extracted with ethyl acetate (2×100 mL). The extracts were combined, dried over anhydrous sodium sulfate, filtered and evaporated. The resulting solid was recrystallized to purity from ether, mp 190°-192° C., to afford N-[2,4-bis(methylthio)-6-methyl-pyridin-3-yl]-2-chloroacetamide (0.39 g, 1.41 mmol, 75%). 1H NMR (CDCl3): δ 7.69 (1H, br s); 6.68 (1H, s); 4.26 (2H, s); 2.53 (3H, s); 2.51 (3H, s); 2.43 (3H, s). Mass spectrum (NH3 -CI/DDIP): m/z 279 (42%); 278 (17%); 277 (100%); 227 (4%). |