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Here is a chemical reaction formula: Reactants are m2:FC(C(=O)O)(F)F, amount is: 0.0 ;m1_m3:C(C(=O)C1=CC=CC=C1)CNC1=C(N(C2=CC(=CC=C12)F)C(=O)OC(C)(C)C)C(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(Cl)Cl, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)CNC1=C(NC2=CC(=CC=C12)F)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(phenacyl)methylamino]-2-carbethoxy-6-fluoro-1-(tert-butyloxycarbonyl)-indole from above in methylene chloride (10 mL). Add trifluoracetic acid (3mL) and stir for 4 hours at room temperature. Dilute with ethyl acetate (50mL) and rinse with 1N sodium hydroxide, saturated sodium chloride, dry overmagnesium sulfate, filter and concentrate in vacuo to yield 3-[(phenacyl)methylamino]-2-carbethoxy-6-fluoroindole. |
Here is a chemical reaction formula: Reactants are m2_m5:CC(C)([O-])C.[K+], amount is: 0.0 MOLE;m1_m3:C(=O)(OCC)CNC1=C(C#N)C=CC(=C1)C(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(C)(=O)OCC, amount is: 0.0 MOLE;m2_m5:O1CCCC1, amount is: 0.0 MOLE;m1_m3:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=C(NC2=CC(=CC=C12)C(F)(F)F)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 2-(Carbethoxy)methylamino-4-trifluoromethylbenzonitrile (2.34 g, 8.6 mmol) in tetrahydrofuran (40 mL) and add dropwise with stirring to a solution of potassium tert-butoxide (9.46 mL of a 1M tetrahydrofuran solution) under a nitrogen atmosphere at 0° C. The reaction was allowed to warm to room temperature. After 3 hour, dilute with ethyl acetate, rinse with water, saturated sodium chloride, dry magnesium sulfate, filter and concentrate in vacuo. Purify the residue by flash chromatography to yield the 3-amino-2-carbethoxy-6trifluoromethylindole (1.22 g, 52%); mp 204°-210° C. |
Here is a chemical reaction formula: Reactants are m3:C(C1=CC=CC=C1)(=O)Cl, amount is: 0.0 ;m2:C(C)N(CC)CC, amount is: 0.0 ;m1:NC1=C(NC2=CC(=CC=C12)C(F)(F)F)C(=O)OCC, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)NC1=C(NC2=CC(=CC=C12)C(F)(F)F)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Suspend the 3-amino-2-carbethoxy-6-trifluoromethylindole (290 mg, 1.06 mmol) in tetrahydrofuran (30 mL) and add triethylamine (0.150 mL, 1.17 mmol). Add benzoyl chloride (0.136 mL, 1.17 mmol) and stir for 30 minutes at room temperature. Dilute the reaction with ethyl acetate (mL), rinse with 1M HCl, water, dry over magnesium sulfate, filter and concentrate in vacuo. Recrystallize from hot ethyl acetate/hexane to yield 3-[(phenacyl)amino]-2-carbethoxy-6-trifluoromethylindole (230 mg, 56%); mp237°-239° C. |
Here is a chemical reaction formula: Reactants are m2:FC(C(=O)O)(F)F, amount is: 0.0 MOLE;m1_m3:C(C(=O)C1=CC=CC=C1)CNC1=C(N(C2=CC(=CC=C12)C(F)(F)F)C(=O)OC(C)(C)C)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m3:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)CNC1=C(NC2=CC(=CC=C12)C(F)(F)F)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(phenacyl)methylamino]-2-carbethoxy-6-trifluoromethyl-1-(tert-butyloxycarbonyl)indole (200 mg, 0.407 mmol) from above in methylene chloride. Add trifluoracetic acid and stir overnight at room temperature. Concentrate the reaction in vacuo, dilute with ethyl acetate and rinse with saturated sodium bicarbonate, dry over magnesium sulfate, filter and concentrate in vacuo to yield 3-[(phenacyl)methylamino]-2-carbethoxy-6-trifluoromethylindole as a foam (154 mg, 97%). |
Here is a chemical reaction formula: Reactants are m5_m7:C(C)(C)(C)N, amount is: 0.0 ;m1_m6:[N+](=O)([O-])C1=CC(=C(C(=O)O)C=C1)N, amount is: 0.0 ;m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m3:ON1C(CCC1=O)=O, amount is: 0.0 ;m4:CCOC(=O)/N=N/C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m7:O1CCCC1, amount is: 0.0 ;m1_m6:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=C(C(=C(C(=O)N)C=C1)N)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 4-nitro-2-aminobenzoic acid (500 mg, 2.75 mmol) in tetrahydrofuran(10 mL). Add triphenylphosphine (730 mg, 2.75 mL) and N-hydroxysuccinimide (316 mg, 2.75 mmol). Add a solution of diethylazodicarboxylate (0.433 mL,2.75 mmol) and stir at room temperature under nitrogen for 10 minutes. Add tert-butylamine (1.1 mL, 5.5 mmol) in tetrahydrofuran (5 mL) directly to the reaction to yield after workup the 4-nitro-2-amino-tert-butylbenzamide. |
Here is a chemical reaction formula: Reactants are m3:C(C1=CC=CC=C1)(=O)Cl, amount is: 0.6200000047683716 MILLIMOLE;m2:C(C)N(CC)CC, amount is: 0.6200000047683716 MILLIMOLE;m4:C(C)(=O)OCC, amount is: 0.0 MOLE;m1:NC1=C(NC2=CC(=CC=C12)[N+](=O)[O-])C(=O)OCC, amount is: 0.6000000238418579 MILLIMOLE,this reaction does not need reagents,Solvents are m5:O1CCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)NC1=C(NC2=CC(=CC=C12)[N+](=O)[O-])C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Suspend the 3-amino-2-carbethoxy-6-nitroindole (0.6 mmol) in tetrahydrofuran (mL) and add triethylamine (0.62 mmol). Add benzoyl chloride (0.62 mmol) and stir for 30 minutes at room temperature. Dilute the reaction with ethyl acetate, rinse with 1M HCl, water, dry over magnesium sulfate, filter and concentrate in vacuo. Recrystallize from hotethyl acetate/hexane to yield 3-[(phenacyl)amino]-2-carbethoxy-6-nitroindole. |
Here is a chemical reaction formula: Reactants are m2:FC(C(=O)O)(F)F, amount is: 0.0 MOLE;m1_m3:C(C(=O)C1=CC=CC=C1)CNC1=C(N(C2=CC(=CC=C12)[N+](=O)[O-])C(=O)OC(C)(C)C)C(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m3:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)CNC1=C(NC2=CC(=CC=C12)[N+](=O)[O-])C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(phenacyl)methylamino]-2-carbethoxy-6-nitro-1-(tert-butyloxycarbonyl)-indole from above in methylene chloride. Add excess trifluoracetic acid and stir overnight at room temperature. Concentrate the reaction in vacuo, dilute with ethyl acetate and rinse with saturated sodium bicarbonate, dryover magnesium sulfate, filter and concentrate in vacuo to yield 3-[(phenacyl)methylamino]-2-carbethoxy-6-nitroindole. |
Here is a chemical reaction formula: Reactants are m4:C(=O)=O, amount is: 0.0 MOLE;m1_m5:[N+](=O)([O-])C1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 MOLE;m2:O.O.[Sn](Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C(C)OCC, amount is: 0.0 MOLE;m7_m6:C(C)O, amount is: 0.0 MOLE;m7_m6:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-nitro-2-carbethoxy-4,6-dichloroindole (38.1 g) in ethanol (1L) and add tin (II) chloride dihydrate (163 g). Warm to between 65° and 75° C. for 4 to 5 hours. Cool to room temperature and pour intoa mixture of ethyl acetate (3L) and water (2L). Add solid potassium carbonate and stir occasionally until the carbon dioxide evolution ceases.Filter through Celite and separate the organic phase of the filtrate. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compoundas an off-yellow solid (33.5 g, 97.6%). |
Here is a chemical reaction formula: Reactants are m2:C(C)N(CC)CC, amount is: 0.0 ;m1_m4:NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m3:C(C1=CC=CC=C1)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)(=O)OCC, amount is: 0.0 ;m1_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (7.8 g, 27.8 mmol) in methylene chloride (500 mL) and add triethylamine (4.2 mL, 30 mmol) followed by benzoyl chloride (3.5 mL, 30 mmol). Stir at room temperature overnight. Dilute with ethyl acetate (300 mL), wash with water and separate the organic phase. Dry (MgSO4) and evaporate the solvent in vacuo to give a solid. Recrystallize (ethyl acetate) to give the title compound as off-white needles (7.75 g, 74%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m6:C(C(=O)C1=CC=CC=C1)NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m1_m2_m3_m6:O.[OH-].[Li+], amount is: 2.390000104904175 MILLIMOLE;m1_m2_m3_m6:O1CCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m6:O, amount is: 0.0 ;m4_m5:O, amount is: 0.0 MOLE;m4_m5:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 3-[(phenacyl)amino]-2-carbethoxy-4,6-dichloroindole (300 mg, 0.79 mmol), lithium hydroxide monohydrate (2.39 mmol), tetrahydrofuran (2 mL) and water (2 mL). Stir at room temperature overnight. Dilute with water and ethyl acetate. Acidify the aqueous phase and separate the organic phase. Dry (MgSO4), evaporate the solvent in vacuo, and recrystallizethe residue (ethyl acetate/hexane) to give the title compound (175 mg, 64%). |
Here is a chemical reaction formula: Reactants are m2:FC(C(=O)O)(F)F, amount is: 0.0 ;m1_m3:C(C(=O)C1=CC=CC=C1)CNC1=C(N(C2=CC(=CC(=C12)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC, 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:C(C(=O)C1=CC=CC=C1)CNC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(phenacyl)methylamino]-2-carbethoxy-4,6-dichloro-1-(tert-butyloxycarbonyl)-indole (2.8 g, 5.7 mmol) in methylene chloride (5 mL). Add trifluoroacetic acid (5 mL) and stir for 1 hour. Evaporate to dryness in vacuo and recrystallize the residue (ethyl acetate/hexane) to give the title compound as white needles (1.8 g, 82%); mp 195°-97° C. |
Here is a chemical reaction formula: Reactants are m3:C(C)I, amount is: 0.0 ;m5:CN(C=O)C, amount is: 0.0 MOLE;m1:[H-].[Na+], amount is: 0.0 MOLE;m4_m7:Cl, amount is: 0.0 ;m2:C(C(=O)C1=CC=CC=C1)NC1=C(N(C2=CC(=CC(=C12)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC, amount is: 0.0 ;m6:CN(C=O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4_m7:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)CCNC1=C(N(C2=CC(=CC(=C12)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Suspend sodium hydride (52 mg of a 60% dispersion, 1.73 mmol) in anhydrous dimethylformamide and cool to -10° C. Add, by dropwise addition, a solution of 3-[(phenacyl)amino]-2-carbethoxy-4,6-dichloro-1-tert-butyloxycarbonyl-indole (0.75 g, 1.57 mmol) in dimethylformamide. Stir under a nitrogen atmosphere for 30 minutes. Add ethyl iodide (0.27 g, 1.73 mmol) and stir at -10° C. for 5 hours. Pour into 1N hydrochloric acid (100 mL) andextract into ethyl acetate. Separate the organic phase and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography (4:1 methylene chloride/ethyl acetate and recrystallize (ethyl acetate/hexane) to give the title compound; mp 110°-11° C. |
Here is a chemical reaction formula: Reactants are m1_m4:C(C(=O)C1=CC=CC=C1)CCNC1=C(N(C2=CC(=CC(=C12)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC, amount is: 0.0 ;m3:C(O)([O-])=O.[Na+], amount is: 0.0 ;m2:FC(C(=O)O)(F)F, 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(=O)C1=CC=CC=C1)CCNC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(phenacyl)ethylamino]-2-carbethoxy-4,6-dichloro-1-tert-butyloxycarbonyl-indole (0.79 g, 1.57 mmol) in methylene chloride (5 mL) and add, by dropwise addition, trifluoroacetic acid (5 mL). Stir for 4 hours and pour carefully into saturated sodium hydrogen carbonate (100 mL). Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo to giveas yellow oil. Recrystallize (ethyl acetate/hexane) to give the title compound (0.23 g, 36%); mp 203°-5° C. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 ;m1_m2_m5:C(C(=O)C1=CC=CC=C1)CCNC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m1_m2_m5:O, amount is: 0.0 ;m3:O.[OH-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)CCNC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 3-[(phenacyl)ethylamino]-2-carbethoxy-4,6-dichloroindole (600 mg, 1.48 mmol), water (10 mL) and tetrahydrofuran (10 mL). Add lithium hydroxide monohydrate (0.22 g, 5.18 mmol) and stir at room temperature for 24 hours.Heat to reflux for 5 hours then pour into 1N hydrochloric acid (100 mL). Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo to give the crude product (0.72 g) as a white solid. Recrystallize (ethyl acetate/hexane) to give the title compound (0.32 g, 57%); mp 254°-6° C. |
Here is a chemical reaction formula: Reactants are m1:[H-].[Na+], amount is: 0.0 MOLE;m3:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m2:C(C(=O)C1=CC=CC=C1)NC1=C(N(C2=CC(=CC(=C12)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:CN(C=O)C, amount is: 0.0 MOLE;m5:CN(C=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)N(C1=C(N(C2=CC(=CC(=C12)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Suspend sodium hydride (42 mg of a 60% dispersion, 1.39 mmol) in dimethylformamide, place under nitrogen atmosphere and cool to -10°C. Add, by dropwise addition, a solution of 3-[(phenacyl)amino]-2-carbethoxy-4,6-dichloro-1-tert-butyloxycarbonyl-indole (0.6 g, 1.26 mmol) in dimethylformamide. Stir at -10° C. for 30 minutes and add, by dropwise addition, benzyl bromide (0.24 g, 1.39 mmol).Stir for 5 hours, pour into 1N hydrochloric acid and extract into ethyl acetate. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as a yellow oil. |
Here is a chemical reaction formula: Reactants are m3:C(O)([O-])=O.[Na+], amount is: 0.0 ;m1_m4:C(C(=O)C1=CC=CC=C1)N(C1C(N(C2=CC(=CC=C12)Cl)C(=O)OC(C)(C)C)(Cl)C(=O)OCC)CC1=CC=CC=C1, amount is: 0.0 ;m1_m4:C(Cl)Cl, amount is: 0.0 ;m2:FC(C(=O)O)(F)F, 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)N(C1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(phenacyl)benzylamino]-2-carbethoxy-2,6-dichloro-1-tert-butyloxycarbonyl-indole (0.68 g, 1.26 mmol) in methylene chloride (5 mL) and add, by dropwise addition, trifluoroacetic acid (5 mL). Stir for 4 hours then slowly add to saturated sodium hydrogen carbonate (100 mL). Extract into methylene chloride, dry (MgSO4) and evaporate the solvent in vacuo. Recrystallize (ethyl acetate/hexane) to give the title compound (0.34 g, 59%); mp 174°-5° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m5:C(C(=O)C1=CC=CC=C1)N(C1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC)CC1=CC=CC=C1, amount is: 0.0 ;m2:O.[OH-].[Li+], amount is: 0.0 ;m3:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5:O1CCCC1, amount is: 0.0 ;m1_m4_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)N(C1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)O)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(phenacyl)benzylamino]-2-carbethoxy-4,6-dichloroindole (0.5 g, 1.07 mmol) in tetrahydrofuran (10 mL) and water (10 mL). Add lithium hydroxide monohydrate (0.16 g, 3.74 mmol) and stir for 24 hours. Heat at reflux for 6 hours and pour into 1N hydrochloric acid (100 mL). Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo. Recrystallize (ethyl acetate/hexane) to give the title compound; mp 266°-7° C. |
Here is a chemical reaction formula: Reactants are m1_m4:C(C(=O)C1=CC=CC=C1)CCOC(=O)CNC1=C(N(C2=CC(=CC(=C12)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC, amount is: 0.0 ;m3:C(O)([O-])=O.[Na+], amount is: 0.0 ;m2:FC(C(=O)O)(F)F, 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(=O)C1=CC=CC=C1)CCOC(=O)CNC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(phenacyl)carbethoxymethyl-amino]-2-carbethoxy-4,6-dichloro-1-tert-butyloxycarbonyl-indole (0.4 g, 0.71 mmol) in methylene chloride (6 mL) and add, by dropwise addition, trifluoroacetic acid (6 mL). Stir for 3.5 hoursand pour slowly into saturated sodium hydrogen carbonate (100 mL). Extract with ethyl acetate and dry (MgSO4). Evaporate the solvent in vacuo and recrystallize the residue (ethyl acetate/hexane) to give the title compound (0.28 g, 85%); mp 139°-40° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m5:C(C1=CC=CC=C1)C1=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=CC=C1, amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE;m2:O.[OH-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5:O1CCCC1, amount is: 0.0 ;m1_m4_m5:O, amount is: 0.0 ;m6_m7:O, amount is: 0.0 ;m6_m7:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)C1=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)O)=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(2-benzylphenacyl)amino]-2-carbethoxy-4,6-dichloroindole (100 mg, 0.214 mmol) in tetrahydrofuran (7 mL) and water (7 mL). Add lithium hydroxide monohydrate (25.2 mg, 6 mmol) and stir overnight. Stir at 40° C. for 2 hours, dilute with water (10 mL) and ethyl acetate (25mL). Acidify with 1N hydrochloric acid while stirring. Separate the organicphase, dry (MgSO4) and evaporate the solvent in vacuo. Recrystallize (ether/hexane) to give the title compound (89 mg, 95%); mp 234°-235° C. |
Here is a chemical reaction formula: Reactants are m2:O.[OH-].[Li+], amount is: 1.2000000476837158 MILLIMOLE;m3:O.[OH-].[Li+], amount is: 1.2000000476837158 MILLIMOLE;m1_m5:C(C1=CC=CC=C1)C1=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=CC=C1, amount is: 0.0 ;m4:O.[OH-].[Li+], amount is: 2.4000000953674316 MILLIMOLE,this reaction does not need reagents,Solvents are m7:O1CCCC1, amount is: 0.0 MOLE;m6:O, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ;m8:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)C1=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)O)=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(2-benzylphenacyl)methylamino]-2-carbethoxy-4,6-dichloroindole (200 mg, 0.41 mmol) in tetrahydrofuran (3 mL) and add water (3 mL). Add lithium hydroxide monohydrate (1.2 mmol) and heat at 60° C. overnight. Add addition lithium hydroxide monohydrate (1.2 mmol) and heat at 60° C. for 5 hours. Allow some of the tetrahydrofuran to evaporate and add methanol to form a homogeneous solution. Heat for 3 days, adding additional lithium hydroxide monohydrate (2.4 mmol). Dilute with water and filter. Acidify, extract into ethyl acetate and dry (MgSO4). Evaporate the solvent in vacuo and recrystallize (ethyl acetate/hexane) to give the title compound as a white powder (180 mg, 97%); mp 280°-83° C. |
Here is a chemical reaction formula: Reactants are m1_m7:NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m3:C(C)N(CC)CC, amount is: 0.0 ;m2:FC1=CC=C(C(=O)Cl)C=C1, amount is: 0.0 ;m4_m5:FC1=CC=C(C(=O)Cl)C=C1, amount is: 0.0 ;m4_m5:C(C)N(CC)CC, amount is: 0.0 ;m6:CCCCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m7:C(Cl)Cl, amount is: 0.0 ;m9:C(C)(=O)OCC, amount is: 0.0 MOLE;m8:C(C)OC(C)=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (2.0 g, 7.13 mmol) in methylene chloride (125 mL) and add p-fluorobenzoyl chloride (0.886 mL, 7.5 mmol) followed by triethylamine (1.05 mL, 7.5 mmol). Stir the reactionat room temperature overnight. Add an additional amount of p-fluorobenzoyl chloride (0.20 mL) and triethylamine (0.20 mL) and stir for 6 hours. Dilute the reaction with ethyl acetate, wash with 1N HCl, saturated sodiumbicarbonate, saturated sodium chloride, dry over magnesium sulfate, filter and concentrate, in vacuo to give a solid. Dissolve the solid in hot ethylacetate (250 mL), reduce to 200 mL and add hot hexane (50 mL). Cool the solution and collect to resulting solid to yield the title compound as fluffy white crystals (1.52 g, 53%); 241°-243° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m7:FC1=CC=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=C1, amount is: 0.0 ;m1_m2_m3_m7:[OH-].[Li+], amount is: 0.0 ;m1_m2_m3_m7:O1CCCC1, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5_m6:O, amount is: 0.0 ;m5_m6:C(C)(=O)OCC, amount is: 0.0 ;m1_m2_m3_m7:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)O)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 3-[(p-fluorophenacyl)amino]-2-carbethoxy-4,6-dichloroindole (600 mg, 1.52 mmol), lithium hydroxide (191 mg, 4.55 mmol), tetrahydrofuran (20 mL)and water (20 mL). Stir overnight at room temperature. Dilute with water (20 mL) and ethyl acetate (40 mL). Acidify with 1N HCl while stirring and separate the layers. Dry the organic phase over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue (ethyl acetate/hexane)to yield the title compound as a white powder (440 mg, 79%); mp 259°-261° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m5:FC1=CC=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=C1, amount is: 0.0 ;m2:[OH-].[Li+], amount is: 0.0 ;m6_m3:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5:O1CCCC1, amount is: 0.0 ;m1_m4_m5:O, amount is: 0.0 ;m6_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)O)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(p-fluorophenacyl)methylamino]-2-carbethoxy-4,6-dichloroindole (660 mg, 1.61 mmol) in tetrahydrofuran (5 mL) and water (5 mL). Add lithium hydroxide (203 mg, 4.8 mmol) and stir for 24 hours at room temperature. Dilute the reaction with water (20 mL) and ethyl acetate (50 mL) and acidify. Separate the layers and dry the organic phase over magnesium sulfate, filter and dilute the filtrate with hexane (100 mL). Recrystallize from this solution to yield the title compound as a white powder (550 mg, 90%). |
Here is a chemical reaction formula: Reactants are m1_m5:NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 ;m3:FC1=C(C(=O)Cl)C=CC=C1, amount is: 0.0 ;m2:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(Cl)Cl, amount is: 0.0 ;m1_m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (1.09 g, 4 mmol) in methylene chloride (25 mL) and add triethylamine (0.578 mL, 4 mmol) followed by o-fluorobenzoyl chloride (1 g, 4 mmol). Stir the reaction for 1 hour at room temperature. Add an additional amount of methylene chloride(25 mL) and stir overnight. Dilute the reaction with ethyl acetate (100 mL), wash with water (100 mL) and dry the organic phase. Concentrate in vacuo and recrystallize the residue from ethyl acetate/hexane to yield thetitle compound (1.05 g, 67%); mp >290° C. |
Here is a chemical reaction formula: Reactants are m1_m3:FC1=C(C(CCNC2=C(N(C3=CC(=CC(=C23)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC)=O)C=CC=C1, amount is: 0.0 MOLE;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 ;m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(o-fluorophenacyl)methylamino]-2-carbethoxy-4,6-dichloro-1-(tert-butyloxycarbonyl)-indole from above in methylene chloride (5 mL). Add trifluoracetic acid (3 mL) and stir for 5 hours. Concentrate the reaction in vacuo, dilute with ethyl acetate (100 mL), wash with saturated sodium carbonate, dry over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue from ethyl acetate/hexane to yield the title compound (650 mg). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC1=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:[OH-].[Li+], amount is: 0.0 ;m1_m2_m3_m4:O1CCCC1, amount is: 0.0 ;m1_m2_m3_m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)O)=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 3-[(o-fluorophenacyl)methylamino]-2-carbethoxy-4,6-dichloroindole (600 mg, 1.47 mmol), lithium hydroxide (184 mg, 4.4 mmol), tetrahydrofuran (10 mL) and water (10 mL). Stir for 24 hours at room temperature. Dilute with ethyl acetate (40 mL). Acidify while stirring and separate the layers. Drythe organic phase over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue (ethyl acetate/hexane) to yield the title compound as a white powder (480 mg, 86%). |
Here is a chemical reaction formula: Reactants are m2:C(C)N(CC)CC, amount is: 0.0 ;m3:FC=1C=C(C(=O)Cl)C=CC1, amount is: 0.0 ;m1_m5:NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(Cl)Cl, amount is: 0.0 ;m1_m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (1.09 g, 4 mmol) in methylene chloride (25 mL) and add triethylamine (0.578 mL, 4 mmol) followed by m-fluorobenzoyl chloride (0.488 mL, 4 mmol). Stir the reactionfor 1 hour at room temperature. Add an additional amount of methylene chloride (25 mL) and stir overnight. Dilute the reaction with ethyl acetate (100 mL), wash with water (100 mL) and dry the organic phase. Concentrate in vacuo and recrystallize the residue from ethyl acetate/hexane to yield the title compound (1.28 g, 81%); mp 234°-235° C. |
Here is a chemical reaction formula: Reactants are m1_m3:FC=1C=C(C(CCNC2=C(N(C3=CC(=CC(=C23)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC)=O)C=CC1, amount is: 0.0 MOLE;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 ;m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(m-fluorophenacyl)methylamino]-2-carbethoxy-4,6-dichloro-1-(tert-butyloxycarbonyl)-indole from above in methylene chloride (5 mL). Add trifluoracetic acid (3 mL) and stir for 5 hours. Concentrate the reaction in vacuo, dilute with ethyl acetate (100 mL), wash with saturated sodium carbonate, dry over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue from ethyl acetate/hexane to yield the title compound (760 mg). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC=1C=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=CC1, amount is: 0.0 ;m1_m2_m3_m4:[OH-].[Li+], amount is: 0.0 ;m1_m2_m3_m4:O1CCCC1, amount is: 0.0 ;m1_m2_m3_m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)OC(C)=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)O)=O)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 3-[(m-fluorophenacyl)methylamino]-2-carbethoxy-4,6-dichloroindole (700 mg, 1.7 mmol), lithium hydroxide (210 mg, 5 mmol), tetrahydrofuran (10 mL)and water (10 mL). Stir for 24 hours at room temperature. Dilute with ethylacetate (40 mL). Acidify while stirring and separate the layers. Dry the organic phase over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue (ethyl acetate/hexane) to yield the title compound as a white powder (590 mg, 91%); mp 270°-280° C. |
Here is a chemical reaction formula: Reactants are m2:FC(C(=O)O)(F)F, amount is: 0.0 ;m1_m3:FC(C1=CC=C(C(CCNC2=C(N(C3=CC(=CC(=C23)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC)=O)C=C1)(F)F, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(Cl)Cl, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C1=CC=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=C1)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(p-trifluoromethylphenacyl)methylamino]-2-carbethoxy-4,6-dichloro-1-(tert-butyloxycarbonyl)-indole from above in methylene chloride (5 mL). Add trifluoracetic acid (3 mL) and stir for 5 hours. Concentrate the reaction in vacuo, dilute with ethyl acetate (100 mL), wash with saturated sodium carbonate, dry over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue from ethyl acetate/hexane to yield the title compound (820 mg). |
Here is a chemical reaction formula: Reactants are m2:C(C)N(CC)CC, amount is: 0.0 ;m1_m5:NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m3:ClC1=CC=C(C(=O)Cl)C=C1, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (2.2 g, 8 mmol) in methylene chloride (70 mL) and add triethylamine (1.16 mL, 8 mmol) followed by p-chlorobenzoyl chloride (0.976 mL, 8 mmol). Stir the reaction48 hours at room temperature. Dilute the reaction with ethyl acetate (300 mL), wash with water (100 mL), dry the organic phase over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue from ethyl acetate/hexane to yield the title compound as a fluffy solid (2.7 g,79%). |
Here is a chemical reaction formula: Reactants are m5:O1CCCC1.CN(C=O)C, amount is: 0.0 ;m2:ClC1=CC=C(C(CNC2=C(N(C3=CC(=CC(=C23)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC)=O)C=C1, amount is: 0.0 ;m3:CI, amount is: 0.0 ;m4:O1CCCC1.CN(C=O)C, amount is: 0.0 ;m1:[H-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(CCNC2=C(N(C3=CC(=CC(=C23)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Suspend sodium hydride (160 mg of a 60% dispersion, 4 mmol) in anhydrous tetrahydrofuran/dimethylformamide (3 mL/2:1) and cool to 0° C. under a nitrogen atmosphere. Add 3-[(p-chlorophenacyl)amino]-2-carbethoxy-4,6-dichloro-1-(tert-butyloxycarbonyl)-indole (2 g, 3.9 mmol) in tetrahydrofuran/dimethylformamide (10 mL/2:1) dropwise to the suspension. Stir at 0° C. for 30 minutes. Add methyl iodide (0.137 mL, 2.2 mmol) and stir for 30 minutes at 0° C. Warm the reaction to room temperature and after 4 hours quench with water (20 mL). Extract with ethyl acetate (20 mL), wash with saturated sodium chloride, dry over magnesium sulfate, filter and concentrate in vacuo to yield the title compound. |
Here is a chemical reaction formula: Reactants are m1_m3:ClC1=CC=C(C(CCNC2=C(N(C3=CC(=CC(=C23)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC)=O)C=C1, amount is: 0.0 MOLE;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 ;m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(p-chlorophenacyl)methylamino]-2-carbethoxy-4,6-dichloro-1-(tert-butyloxycarbonyl)-indole from above in methylene chloride (15 mL). Add trifluoracetic acid (5 mL) and stir for 5 hours. Concentrate the reaction in vacuo, dilute with ethyl acetate (100 mL), wash with saturated sodium carbonate, dry over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue from ethyl acetate/hexane to yield the title compound (1.3 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=CC=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=C1, amount is: 0.0 ;m1_m2_m3_m4:[OH-].[Li+], amount is: 0.0 MOLE;m1_m2_m3_m4:O1CCCC1, amount is: 0.0 MOLE;m1_m2_m3_m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC=C(C(CCNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)O)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 3-[(p-chlorophenacyl)methylamino]-2-carbethoxy-4,6-dichloroindole (1.3 g, 3.1 mmol), excess lithium hydroxide, tetrahydrofuran and water and stirovernight. Dilute with ethyl acetate and separate the layers. Dry the organic phase over magnesium sulfate, filter and concentrate in vacuo to yield the title compound; mp 279°-283° C. |
Here is a chemical reaction formula: Reactants are m2:C1(=CC=CC=C1)S(=O)(=O)Cl, amount is: 0.0 ;m1_m3:NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)S(=O)(=O)NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 3-amino-2-carbethoxy-4,6-dichloroindole (3.31 g, 12.1 mmol) and anhydrous pyridine (50 mL). Add, by dropwise addition, phenylsulfonyl chloride (2.35 g, 13.33 mmol). Stir for 48 hours at room temperature. Pourinto 1N hydrochloric acid (500 mL), extract with ethyl acetate and dry (MgSO4). Evaporate the solvent in vacuo and recrystallize (ethyl acetate/hexane) to give the title compound (3.15 g, 63%); mp 245°-7° C. |
Here is a chemical reaction formula: Reactants are m3:O.[OH-].[Li+], amount is: 0.0 ;m1_m2_m6:C1(=CC=CC=C1)S(=O)(=O)NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m1_m2_m6:O1CCCC1, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE;m1_m2_m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)S(=O)(=O)NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 3-[(phenylsulfonyl)amino]-2-carbethoxy-4,6-dichloroindole (0.35 g, 0,847 mmol), tetrahydrofuran (10 mL) and water (7 mL). Add lithium hydroxide monohydrate (0.11 g, 2.54 mmol) and stir at room temperature overnight. Warm at 65° C. for 5 hours, pour into water and acidify to pH 1 with 1N hydrochloric acid. Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo. Recrystallize (ethyl acetate/hexane) to give the title compound (0.2 g, 61%); mp 229°-35° C. (dec). |
Here is a chemical reaction formula: Reactants are m2:FC(C(=O)O)(F)F, amount is: 0.0 ;m1_m3:C1(=CC=CC=C1)S(=O)(=O)CNC1=C(NC2=CC(=C(C(=C12)Cl)C(=O)OC(C)(C)C)Cl)C(=O)OCC, 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:C1(=CC=CC=C1)S(=O)(=O)CNC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(phenylsulfonyl)methylamino]-2-carbethoxy-4,6-dichloro-tert-butyloxycarbonyl-indole (400 mg, 0.758 mmol) in methylene chloride (15 mL). Add, by dropwise addition, trifluoroacetic acid (15 mL) and stir at room temperature for 3 hours. Evaporate the solvent in vacuo and treat the resulting residue with saturated sodium hydrogen carbonate. Extract into methylene chloride and dry (MgSO4). Recrystallize (ethyl acetate/hexane) to give the title compound (70 mg, 22%); mp 244°-45° C. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 ;m3:O.[OH-].[Li+], amount is: 2.5999999046325684 MILLIMOLE;m1_m2_m5:C1(=CC=CC=C1)S(=O)(=O)CNC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m1_m2_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)S(=O)(=O)CNC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 3-[(phenylsulfonyl)methylamino]-2-carbethoxy-4,6-dichloroindole (185 mg, 0.433 mmol), tetrahydrofuran (25 mL) and water (25 mL). Add lithium hydroxide monohydrate (2.6 mmol) and stir at room temperature for 3 days, then at reflux for 5 hours. Pour into 1N hydrochloric acid (200 mL) and extract into ethyl acetate. Dry (MgSO4) and evaporate the solvent in vacuo. Recrystallize (ethyl acetate/hexane) to give the title compound (122 mg, 71%); mp 286°-90° C. |
Here is a chemical reaction formula: Reactants are m2:[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1, amount is: 0.0 ;m3:Cl, amount is: 0.0 ;m1_m4:NC1=C(NC2=CC(=CC(=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ;m1_m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (10 g, 36.6 mmol) in anhydrous pyridine (100 mL). Add 4-nitrobenzoyl chloride (7.47 g, 40.27 mmol) and stir for 5 hours. Pour into 1N hydrochloric acid (500 mL) and extract into ethyl acetate. Evaporate the solvent in vacuo and dry at 70° C. under vacuum to give the title compound (15.75 g, 100%); mp 283°-86° C. |
Here is a chemical reaction formula: Reactants are m3:O.[OH-].[Li+], amount is: 0.0 ;m1_m2_m5:[N+](=O)([O-])C1=CC=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)OCC)=O)C=C1, amount is: 0.0 ;m1_m2_m5:O1CCCC1, amount is: 0.0 ;m4:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(CNC2=C(NC3=CC(=CC(=C23)Cl)Cl)C(=O)O)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 3-[(4-nitrophenacyl)amino]-2-carbethoxy-4,6-dichloroindole (161 mg, 0.381 mmol), tetrahydrofuran (20 ml) and water (20 mL). Add lithium hydroxide monohydrate (64 mg, 1.52 mmol) and stir overnight. Heat at reflux for 4 hours, cool to room temperature and pour onto 1N hydrochloricacid (100 mL). Collect the resulting solid by filtration and air dry to give the title compound (148 mg, 99%); mp 270°-72° C. |
Here is a chemical reaction formula: Reactants are m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 MOLE;m4:C(=O)=O, amount is: 0.0 MOLE;m2:O.O.[Sn](Cl)Cl, amount is: 0.0 ;m1_m5:[N+](=O)([O-])C1=C(NC2=CC(=C(C=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C(C)OCC, amount is: 0.0 MOLE;m7_m6:C(C)O, amount is: 0.0 MOLE;m7_m6:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:NC1=C(NC2=CC(=C(C=C12)Cl)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-nitro-2-carbethoxy-5,6-dichloroindole (38.1 g) in ethanol (1L) and add tin (II) chloride dihydrate (163 g). Warm to between 65° and 75° C. for 4 to 5 hours. Cool to room temperature and pour intoa mixture of ethyl acetate (3L) and water (2L). Add solid potassium carbonate and stir occasionally until the carbon dioxide evolution ceases.Filter through diatomaceous earth and separate the organic phase of the filtrate. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound. |
Here is a chemical reaction formula: Reactants are m3:C(C1=CC=CC=C1)(=O)Cl, amount is: 0.0 ;m2:C(C)N(CC)CC, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 ;m1_m5:NC1=C(NC2=CC(=C(C=C12)Cl)Cl)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)NC1=C(NC2=CC(=C(C=C12)Cl)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-amino-2-carbethoxy-5,6-dichloroindole (2.2 g, 8 mmol) in methylene chloride (70 mL) and add triethylamine (1.16 mL, 8 mmol) followed by benzoyl chloride (0.93 mL, 8 mmol). Stir the reaction 48 hoursat room temperature. Dilute the reaction with ethyl acetate (300 mL), wash with water (100 mL), dry the organic phase over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue from ethyl acetate/hexane to yield the title compound. |
Here is a chemical reaction formula: Reactants are m2:FC(C(=O)O)(F)F, amount is: 0.0 ;m1_m3:C(C(=O)C1=CC=CC=C1)CNC1=C(N(C2=CC(=C(C=C12)Cl)Cl)C(=O)OC(C)(C)C)C(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:C(C)(=O)OCC, amount is: 0.0 ;m1_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=O)C1=CC=CC=C1)CNC1=C(NC2=CC(=C(C=C12)Cl)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve 3-[(phenacyl)methylamino]-2-carbethoxy-5,6-dichloro-1-(tert-butyloxycarbonyl)-indole from above in methylene chloride (15 mL). Add trifluoracetic acid (5 mL) and stir for 5 hours. Concentrate the reaction in vacuo, dilute with ethyl acetate (100 mL), wash with saturated sodium carbonate, dry over magnesium sulfate, filter and concentrate in vacuo. Recrystallizethe residue from ethyl acetate/hexane to yield the title compound. |
Here is a chemical reaction formula: Reactants are m3:C(C)Br, amount is: 0.0 ;m2_m5:[Li+].CC(C)[N-]C(C)C, amount is: 0.0 ;m1_m4:C1C(CCC2=CC=CC=C12)=O, amount is: 0.0 ;m1_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:C1CCCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:O=C1C(C2=CC=CC=C2CC1)(CC=C)CC=C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 7.3 g (50 mmol) 2-tetralone in 75 ml THF in a three-neck round-bottomed flask, equipped with a gas inlet and septum, was added 36.7 mL LDA (55 mmol, 1.5M in cyclohexane, at -30° C. under a nitrogen atmosphere. The solution was allowed to warm to 0° C. over a thirty-minute period and 5.6 mL (65 mmol) ethyl bromide was added. TLC analysis was used to monitor the reaction. After stirring for 24 hours at room temperature, the reaction mixture was quenched with 10% sodium bisulfate to pH2-3. After removal of THF under reduced pressure, the mixture was extracted with ethyl acetate (2×1 L) and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by liquid chromatography on 800 g of silica gel 60 (230-400 m), eluting with 1 L hexane, followed by 5 L of 5% ethyl acetate/hexane, and collecting 40 mL fractions. Fractions 41-64 gave 4.2 g (37%) of pure and 1,2,3,4-tetrahydro-2-oxo-1,1-di-(2-propenyl)naphthalene as a colorless oil and fractions 65-82 gave 3.1 g (33%) of pure 1,2,3,4-tetrahydro-2-oxo-1-(2-propenyl)-naphthalene as a light yellow oil. |
Here is a chemical reaction formula: Reactants are m2:[Li+].CC(C)[N-]C(C)C, amount is: 0.0 ;m3:BrCC(=O)OC, amount is: 0.0 ;m1_m4:C1CC2=CC=CC=C2CC1=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(CC1C(CCC2=CC=CC=C12)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A three-neck, round-bottomed flask equipped with a dropping funnel and a septum, was charged with 6.6 mL (50 mmol) of beta-tetralone and 100 mL of THF under a nitrogen atmosphere. The solution was cooled to -30° C. and 36.6 mL (55 mmol) of LDA (1.5M in cyclohexane) was added dropwise. The solution was stirred for 30 minutes and warmed to 0° C. To this solution, 5.7 mL (60 mmol) of methyl bromoacetate was added. The solution was stirred at 0° C. for 1 h. The reaction was quenched with 3N HCl until pH of the mixture was <3. THF was removed in vacuo and the concentrate was extracted with methylene chloride (2×500 mL). The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil. This oil was purified by liquid chromatography on 560 g silica gel 60 (230°-400 m), eluting with hexane-ethyl acetate (4:1) and collecting 40 mL fractions. Fractions homogeneous by TLC were combined and concentrated in vacuo. The resulting oil needed the second chromatography to afford 8.22 g (75.4%) of >95% pure product as a near colorless oil. |
Here is a chemical reaction formula: Reactants are m1_m4:COC=1C=CC=C2CCC(CC12)=O, amount is: 0.0 ;m2:[Li+].CC(C)[N-]C(C)C, amount is: 0.0 ;m3:BrC(C(=O)OC)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(CCC1C(CCC2=CC=CC(=C12)OC)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A three-neck, round-bottomed flask, equipped with a dropping funnel and septum, was charged with 1.76 g (10 mmol) of 8-methoxy-2-tetralone and 20 mL of THF under a nitrogen atmosphere. The solution was cooled to -30° C. and 7.5 mL (11 mmol) of LDA (1.5M in cyclohexane) was added dropwise. The solution was stirred for 30 minutes and warmed to 0° C. To this solution, 1.3 mL (12 mmol) of methyl bromopropionate was added. The solution was stirred at room temperature for two hours. The reaction was quenched with 3 N HCl until pH of the mixture was <3. THF was removed in vacuo and the concentrate was extracted with methylene chloride (2×500 mL). The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil. This oil was purified by liquid chromatography on 400 g silica gel 60 (230-400 m), eluting with hexane-acetone (4:1), and collecting 40 mL fractions. Fractions homogeneous by TLC were combined and concentrated in vacuo to give 1.63 g (63%) of the title compound as a yellow oil. |
Here is a chemical reaction formula: Reactants are m1:IC1=C(C(=NC=C1)OC)C=O, amount is: 0.0 ;m5:C([O-])(O)=O.[Na+], amount is: 0.0 ;m2_m3:C(C=CC)O, amount is: 0.0 ;m2_m3:C(C)[SiH](CC)CC, amount is: 0.0 ;m4:FC(C(=O)O)(F)F, 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=CC)OCC=1C(=NC=CC1I)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 500 mL 3-necked round-bottom flask equipped with an overhead mechanical stirrer and under nitrogen, is charged with 4-iodo-2-methoxy-pyridine-3-carbaldehyde (75.0 g, 0.29 mol) as prepared in example 1, crotyl alcohol (75 mL, 0.88 mol), and triethylsilane (70 mL, 0.44 mol). To the stirred suspension at 0° C. is added trifluoroacetic acid (175 mL, 2.27 mol) dropwise via an addition funnel. The resulting solution is stirred at about 22° C. for approximately 12 hr. The reaction mixture is slowly poured into a rapidly stirring saturated sodium bicarbonate solution (2 L). The mixture is extracted with 3×500 mL of hexane. The combined organic layers are dried over sodium sulfate, filtered, and concentrated in vacuo to give an oil. Purification of this oil by vacuum distillation (ca. 0.4 mm Hg, ca. 120°-130° C.) yields 3-(but-2-enyloxymethyl)-4-iodo-2-methoxy-pyridine as a pale yellow oil: 1H-NMR (400 MHz, CDCl3) δ7.69 (d, J=5 Hz, 1H), 7.34 (d, J=5 Hz, 1H), 5.71 (m, 2H), 4.58 (s, 2H), 4.02 (d, J=1 Hz, 2H), 3.94 (s, 3H), 1.72(d, J=6 Hz, 3H); IR (neat) 2948, 2859, 1561, 1459, 1381, 1361, 1301, 1233, 1169, 1094, 1052 cm-1 ; Elemental analysis: calculated for C11H14NO2I: C 41.40, H 4.42, N 4.39, I 39.76; Found: C 41.31, H 4.45, N 4.37, I 39.71. |
Here is a chemical reaction formula: Reactants are m4:FC(C(=O)O)(F)F, amount is: 0.0 ;m2:C(C)[SiH](CC)CC, amount is: 0.0 ;m1:ClC1=CC(=C(C(=N1)OC)C=O)I, amount is: 0.0 ;m3:C(C=CC)O, amount is: 0.0 ;m5_m6:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5_m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC(=C(C(=N1)OC)COCC=CC)I, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 3-necked 500-mL round-bottom flask is equipped with a mechanical stirrer. Under nitrogen, the flask is charged with 6-chloro-4-iodo-2-methoxypyridine-3-carbaldehyde (53.0 g, 178 mmol) obtained as described in U.S. Pat. No. 5,254,690 to Comins et al. issued Oct. 19, 1993 and incorporated herein by reference, triethylsilane (42.7 mL, 267 mmol) and crotyl alcohol (60.8 mL, 713 mmol). The slurry is cooled to 0° C. and trifluoroacetic acid (90.0 mL, 1.17 mmol) is added over 1 h. The reaction is allowed to warm to ambient temperature and stirred for 16 h. The reaction mixture is slowly poured into a rapidly stirred solution of saturated sodium bicarbonate in water (1.5 L). The mixture is extracted with methyl t-butyl ether (4×300 mL). The combined organic layers are washed with brine (700 mL) and dried over anhydrous sodium sulfate (150 g). The drying agent is removed by filtration and the solvents are removed in vacuo to afford 6-chloro-4-iodo-2-methoxy-3-(2-butenyloxymethyl)pyridine as crude product. The product can be purified by vacuum distillation to provide 6-chloro-4-iodo-2-methoxy-3-(2-butenyloxymethyl)pyridine as a light yellow oil. 1H NMR (200 MHz, CDCL3) δ1.75 (d, J=6.1 Hz, 3H), 3.92 (s, 3H), 4.00 (m, 2H), 4.59 (s, 2H), 5.74 (m, 1H), 5.75 (m, 1H), 7.39 (s, 1H). |
Here is a chemical reaction formula: Reactants are m3_m5_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m2:CN(C=O)C, amount is: 0.0 ;m1:C(C=CC)OCC=1C(=NC=CC1I)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCOC(=O)C.CCCCCC, amount is: 0.0 MOLE,Catalysts are m3_m5_m4:[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 ;m3_m5_m4:C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-], amount is: 0.0 .Products are 0:C(C)C1=COCC2=C(N=CC=C21)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 3-liter 3-necked round-bottom flask is equipped with a heating mantle monitored by a J-KEM thermocouple and an overhead stirrer; under nitrogen, the flask is charged with 3-(but-2-enyloxymethyl)-4-iodo-2-methoxy-pyridine (30.0 g, 93.9 mmol), as prepared in example 2, and 939 mL (0.1M) of N,N-dimethylformamide, followed by successive addition of anhydrous potassium carbonate (26.0 g, 188 mmol), palladium(II) acetate (422 mg, 1.88 mmol) and tetrabutylammonium chloride (13.1 g, 47.0 mmol). The light brown mixture is brought to 90° C. and stirred for 30 min. The now dark brown mixture is allowed to cool to 85° C. and stirring is continued for 20 h when TLC (10% EtOAc/hexane) indicates complete reaction. After being cooled to ambient temperature, the mixture is filtered through Celite 545® (80 g), washed with MTBE (0.5 L) and the filtrate is poured into 800 mL of ice water and extracted with MTBE (3×600 mL). The combined extracts are successively washed with water (700 mL) and brine (700 mL), dried over anhydrous Na2SO4 (150 g). Evaporation in vacuo yields crude 4-ethyl-8-methoxy-1H-pyrano[3,4-c]pyridine 1H NMR (400 MHz) indicates an endo/exo ratio of 8:1. Vacuum distillation at, ca. 112°-120° C. yields 4-ethyl-8-methoxy-1H-pyrano[3,4-c]pyridine as an 11:1 endo/exo mixture. 1H-NMR (400 MHz, CDCl3) δ8.04 (d, J=5.4 Hz, 1H), 6.65 (d, J=5.4 Hz, 1H), 6.54 (s, 1H), 5.04 (s, 2H), 3.94 (s, 3H), 2.32 (m, 2H), 0.97 (t, J=7.2 Hz, 3H), HRMS (EI+): calc for C11H13NO2 : 191.0946, Found: 191.0952. IR 3450, 2962, 1731, 1602, 1581, 1454, 1390, 1362, 1313, 1267 cm-1 |
Here is a chemical reaction formula: Reactants are m1:NC=1C(=CC2=C(OCCO2)C1)C(CCl)=O, amount is: 0.0 ;m4_m5:C[O-].[Na+], amount is: 0.0 MOLE;m4_m5:CO, amount is: 0.0 ;m3:CC(C(=O)Cl)C(=O)Cl, amount is: 0.0 ;m2_m7:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m2_m7:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C=1C(NC=2C=C3C(=CC2C1CCl)OCCO3)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 4-necked 12-L round-bottom flask is equipped with a mechanical stirrer and 500-mL addition funnel. Under nitrogen, the flask is charged with 1-(7-amino-2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-chloro-ethanone (595 g, 2.61 mol), as prepared above, triethylamine (474 mL, 3.40 mol), and anhydrous acetonitrile (3.5 L). The solution is cooled to 0° C., then methyl malonyl chloride (364 mL, 3.40 mol) is added over 35 min. The cooling bath is removed and the mixture is stirred for 5 h. To the resultant slurry is added 25% sodium methoxide in methanol (596 mL, 2.61 mol) over 10 min. After being stirred at ambient temperature for 2 h, the now very thick yellow slurry is diluted with water (3 L). The precipitate is collected on a Buchner funnel and washed with water (3 L). The yellow solid is dried in vacuo. at 60° C. yielding 9-chloromethyl-7 -oxo-2,3,6,7-tetrahydro[1,4]dioxino[2,3-g]quinoline-8-carboxylic acid methyl ester as a yellow solid. This crude product is used for the next step without further purification. Recrystallization from MeOH-DMSO (1:1) gave an analytical sample: mp>300° C. (dec.). 1H NMR (DMSO-d6, 400 MHz) δ3.85 (s, 3H), 4.32 (s, 2H), 4.36 (s, 2H), 4.83 (s, 2H), 6.83 (s, 1H), 7.40 (s, 2H), 12.0 (s, 1H). Elemental analysis: Calculated for C10H10ClNO3 : C 54.29, H 3.91, N 4.52. Found: C 53.68, H 3.84, N 4.48. HRMS (EI+): Calculated for C10H10ClNO3 : 309.0404. Found: 309.0405. |
Here is a chemical reaction formula: Reactants are m2:CS(=O)C, amount is: 0.0 ;m1:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m3:ClC1=NC=2C=C3C(=CC2C(=C1CO)CN1CCN(CC1)C)OCCO3, amount is: 0.0 ;m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(Cl)Cl, amount is: 0.0 ;m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=NC=2C=C3C(=CC2C(=C1C=O)CN1CCN(CC1)C)OCCO3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 3-necked 4-L round-bottom flask is equipped with a mechanical stirrer and a 250-mL addition funnel. Under nitrogen, the flask is charged with methylene chloride (800 mL), followed by addition of oxalyl chloride (28.8 mL, 330 mmol). The solution is cooled to -78° C. and dimethyl sulfoxide (46.7 mL, 660 mmol) is added over 6 min. The temperature of the solution increases to -58° C. during the addition and is cooled back to about -70° C. After stirring for 3 min, [7-chloro-9-(4-methyl-piperazin-1-ylmethyl)-2,3-dihydro-[1,4]dioxino[2,3-g]quinolin-8-yl]-methanol (100 g, 275 mmol), as prepared above, is added as a solution in 140 mL of methylene chloride over 10 min. The yellow slurry is stirred for 45 min, then anhydrous triethylamine (153 mL, 1.10 mol) is added over 4 min. Stirring is continued for 10 min at -78° C., then the cooling bath is removed. The reaction mixture is allowed to warm to -5° C. and poured into 2 L of water. The organic layer is separated and the aqueous layer is extracted with methylene chloride (3×1.5 L). The combined organic layers are washed with brine (2 L), dried over anhydrous sodium sulfate and concentrated in vacuo yielding 7-chloro-9-(4-methyl-piperazin-1-ylmethyl)-2,3-dihydro-[1,4 ]dioxino [2,3-g]quinolin-8-carbaldehyde as a dark solid. This crude product is used for the next step without further purification. Recrystallization from CH2Cl2 -MeOH (5:1) provided an analytical sample as a light yellow solid: 140°-142° C. (dec.). 1H NMR (CDCl3, 200 MHz) δ2.30 (s, 3H), 2.45, 2.59 (m, 8H), 3.98 (s, 2H). 4.41(s, 4H), 7.46 (s, 1H), 7.53 (s, 1H), 10.4 (s, 1H). Elemental analysis: Calculated for C18H20ClN3O3 : C 59.75, H 5.57, N 11.61. Found: C 59.78, H 5.62, N 11.64. |
Here is a chemical reaction formula: Reactants are m2:ClC1=NC=2C=C3C(=CC2C(=C1C=O)CN1CCN(CC1)C)OCCO3, amount is: 0.0 ;m1:O, amount is: 0.0 MOLE;m4:Cl, amount is: 0.0 ;m3_m5:[I-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:IC1=NC=2C=C3C(=CC2C(=C1C=O)CN1CCN(CC1)C)OCCO3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 4-necked 12-L round-bottom flask is equipped with a mechanical stirrer and water-cooled condenser. Under nitrogen, the flask is charged with 7-chloro-9-(4-methyl-piperazin-1-ylmethyl)-2,3-dihydro-[1,4]dioxino[2,3-g]quinolin-8-carbaldehyde (120 g, 346 mmol), as prepared above, sodium iodide (1.04 kg, 6.92 mmol), and 3 L of acetonitrile. To the yellow suspension is added concentrated hydrogen chloride (59.7 mL, 726 mmol) over 5 min. The white slurry is refluxed for 15 hr. The solvent is mostly removed by short-path distillation in vacuo. The resultant thick slurry is cooled to ambient temperature and treated with 2.5 L of water and 2.5 L of methylene chloride. The organic layer is separated and the aqueous layer is extracted with methylene chloride (3×2 L). The combined organic layers are washed with brine (2.5 L), dried over anhydrous sodium sulfate, concentrated and dried in vacuo at 30° C. yielding 7-iodo-9-(4-methyl-piperazin-1-ylmethyl)- 2,3-dihydro-[1,4]dioxino[2,3-g]quinolin-8-carbaldehyde as a yellow solid. This crude product is used for the next step without further purification. Recrystallization from CH2Cl2 -MeOH (1:1) gave an analytical sample as an off-white solid: 198°-200° C. (dec.). 1H NMR (CDCl3, 200 MHz) δ2.30 (s, 3H), 2.43, 2.57 (m, 8H), 3.93 (s, 2H). 4.40(s, 4H), 7.47 (s, 1H), 7.50 (s, 1H), 10.1 (s, 1H). Elemental analysis: Calculated for C18H20IN3O3 : C 47.70, H 4.45, N 9.27. Found: C 47.78, H 4.45, N 9.26. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C1=CC=CC=C1)(=O)[O-], amount is: 0.0 MOLE;m1_m2:C(C1=CC=CC=C1)(=O)Cl, 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(C1=CC=CC=C1)(=O)OC(C1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Moreover, in the case of benzoyl chloride, the resulting mixed anhydride is more reactive than benzoyl chloride. Thus, the carboxylate ion of acrylic acid preferentially reacts with the mixed anhydride to give acrylic anhydride and the benzoate ion, which subsequently reacts with unreacted benzoyl chloride to give benzoic anhydride, according to reaction scheme I. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:OCCC1=C(N=CS1)C, amount is: 0.0 ;m1_m2_m3:BrCC(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Br-].C(C)OC(=O)C[N+]1=CSC(=C1C)CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 5-(2-hydroxyethyl)-4-methylthiazole (306 g) and ethyl bromoacetate (356.2 g) in ethanol (1 L) was heated to reflux. After two hours, the ethanol was removed by distillation and the residue treated with isopropanol (1.5 L). The resulting solution was cooled to about 0° C., causing crystallization of compound 1. After three hours, the crystalline material was separated from the mother liquor. Additional crystals were obtained by prolonged cooling of the mother liquor at 0° C. Combination of the crystalline material gave 474.3 g of compound 1. Melting point 96°-98° C. |
Here is a chemical reaction formula: Reactants are m1:C(C1=CC=CC=C1)OC(=O)N1C(C2CCC(C2C1)=O)C(=O)OCC, amount is: 0.0 ;m3:C(CCC)P(CCCC)CCCC, amount is: 0.0 ;m4:OO, amount is: 0.0 ;m5:Cl, amount is: 0.0 ;m2:[N+](=O)([O-])C1=C(C=CC=C1)[Se]C#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O1CCCC1, amount is: 0.0 ;m7:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)N1C(C2C(C=CC2C1)O)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of the compound prepared as described in Example 3 (6.89 g) and 2-nitrophenyl selenocyanate (4.72 g) in tetrahydrofuran (100 ml) was cooled to about -20° C. under a nitrogen atmosphere. The cooled solution was treated with tributylphosphine (5.2 ml) in one portion. After one hour, the reaction solution was treated with pyridine (100 ml) and the resulting mixture allowed to warm to room temperature. The reaction was then treated with 30% hydrogen peroxide (35 ml). After an additional two hours, the reaction mixture was added to 1N hydrochloric acid (200 ml), and the title compound was extracted with diethyl ember. The diethyl ether extracts were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC, eluting with a linear gradient of hexane to hexane/ethyl acetate (1:1), to give 4.97 g of compound 7. |
Here is a chemical reaction formula: Reactants are m1:C(C1=CC=CC=C1)OC(=O)N1C(C2C=CC(C2C1)=O)C(=O)OCC, amount is: 0.0 ;m3:[H][H], amount is: 0.0 MOLE;m2:C(OC)(=O)OC(=O)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O1CCCC1, amount is: 0.0 ,Catalysts are m5:[Pd], amount is: 0.0 .Products are 0:COC(=O)N1C(C2C(CCC2C1)=O)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of the compound prepared as described in Example 5 (4.70 g), dimethyl pyrocarbonate (3.83 g), and 5% palladium/carbon (1.0 g) in tetrahydrofuran (100 ml) was hydrogenated at a hydrogen pressure of 60 psi and at room temperature. After two hours, the catalyst was removed by filtration and the filtrate concentrated in vacuo to give 3.41 g of compound 9. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:CN(C1=CC=C(C=CC=O)C=C1)C, amount is: 0.0 ;m1_m2_m3_m5:CN(C1=CC=C(C=C1)C(C)C1=CC=C(C=C1)N(C)C)C, amount is: 0.0 ;m1_m2_m3_m5:C(C)O, amount is: 0.0 ;m4:CN(C1=CC=C(C=C1)C(C)C1=CC=C(C=C1)N(C)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C1=CC=C(C=C1)C(=CC(C=CC1=CC=C(C=C1)N(C)C)C=C(C1=CC=C(C=C1)N(C)C)C1=CC=C(C=C1)N(C)C)C1=CC=C(C=C1)N(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 5.7 g of 4-dimethylaminocinnamaldehyde, 16.2 g of 1,1-bis(4-dimethylaminophenyl)ethane, 300.0 ml of ethyl alcohol and 6.0 ml of glacial acetic acid was refluxed approximately eighteen hours. After cooling slightly an additional 3.0 g of 1,1-bis(4-dimethylaminophenyl)ethane was added and reflux maintained for an additional four hours. The resulting reaction mixture was cooled to approximately 5° C. and the solid which formed was collected by filtration. The solid was recrystallized from isopropyl alcohol, filtered and dried to obtain 16.3 g of bis{[2,2-bis(4-dimethylaminophenyl)]ethenyl}[2-(4-dimethylaminophenyl)ethenyl]methane (Formula II: R,R1,R3,R4,R9 and R10 =CH3 ; R2, R5 and R11 =H) a yellow solid which melted at 78°-82° C. Significant infrared maxims appeared at 1610 cm-1 (v.s.) and 830 cm-1 (v.s.). An acetone solution of the product spotted onto clay, phenolic resin and organic acid coated papers slowly developed a blue-colored image. Exposure of the spotted papers to bromine vapor increased the speed of color development. |
Here is a chemical reaction formula: Reactants are m5:[Cl-].[K+], amount is: 0.0 MOLE;m6:[Cl-].[Na+], amount is: 0.0 MOLE;m2_m3_m4:[Cl-].[K+], amount is: 0.0 MOLE;m2_m3_m4:[Cl-].[Na+], amount is: 0.0 MOLE;m2_m3_m4:P(=O)([O-])([O-])[O-], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:P(=O)(O)(O)[O-].[K+];0:P(=O)(O)(O)[O-].[Na+], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The fine particles of potassium chloride or sodium chloride and the fine particles of phosphate or a buffering agent may be separately prepared. For example, when a concentrated aqueous solution of potassium chloride or sodium chloride is formed, an aqueous solution of potassium dihydrogen phosphate and sodium dihydrogen phosphate (4:6 in molar ratio) can be separately formed. Both solutions are preferably in a saturation state, which provides a greater amount of fine particles, i.e., a high efficiency. Note that the weighed phosphates must be completely dissolved in water, because the proportion of the dissolved phosphates significantly affects the pH value. The thus-prepared aqueous solutions are poured into an organic solvent such as ethanol, in the same manner as described above, respectively, and the precipitated fine particles are collected. |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m3:CS(=O)(=O)OCCOCCOCCOC, amount is: 0.0 ;m1_m5_m2_m3:IC=1C=C(C=CC1)O, amount is: 0.0 ;m1_m5_m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m4_m7_m0:CCOC(=O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2_m3:CN(C)C=O, amount is: 0.0 ;m4_m7_m0:CCCCCC, amount is: 0.0 MOLE;m6:CN(C)C=O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:IC=1C=C(OCCOCCOCCOC)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1-[(methanesulfonyl)-oxy]-3,6,9-trioxadecane (11.6 g, 47.9 mmol) in dry DMF (145 ml) was added 3-iodophenol (10.6 g, 48.2 mmol) and potassium carbonate (6.6 g, 47.8 mmol). The reaction was immersed in an oil bath which was warmed to 68° C. over a period of 0.5 hr. The reaction was stirred at this temperature under an N2 atmosphere for 16 hrs and then at 82° C. for an additional 2 hrs. At the end of this period, the reaction was cooled, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into ethyl acetate (500 ml), washed with water (200 ml), 1N aqueous sodium hydroxide (200 ml) and brine (200 ml), dried (Na2SO4), filtered and evaporated in vacuo to provide a light brown oil. Flash column chromatography (silica, 1:3 to 1:2; EtOAc:hexane) provided 1 -(3-iodophenoxy)-3,6,9-trioxadecane as a light yellow oil (10.8 g, 37.1%). |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m3_m6:CS(=O)(=O)OCCC(C)OS(=O)(=O)C, amount is: 0.0 ;m1_m2_m5:C=1C(=CC(=C(C1I)O)I)I, amount is: 0.0 ;m1_m2_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:C(C)(=O)OCC, amount is: 0.0 MOLE;m3_m6:CN(C)C=O, amount is: 0.0 ;m1_m2_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:IC1=C(OCCC(C)OC2=C(C=C(C=C2I)I)I)C(=CC(=C1)I)I, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of triiodophenol (5.78 g, 12.3 mmol) and sodium hydride (0.49 g, 60% dispersion, 12.3 mmol) in DMF (15 ml) was stirred at room temperature for 1 hour and then a solution of 1,3-bis-(methanesulfonyloxy) butane (1.37 g, 5.58 mmol) in DMF (5 ml) was added. The mixture was heated to 90° C. for 6 hours and then poured into water after cooling. Ethyl acetate was added and the mixture was allowed to stand overnight. The precipitated solid was collected and dried to give 3.0 g (54%) of the desired product, Mp 173°-175° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m5:IC=1C=C(C=CC1)O, amount is: 0.0 ;m1_m2_m3_m5:IC1=C(OCCCCCCCl)C(=CC(=C1)I)I, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:IC=1C=C(OCCCCCCOC2=C(C=C(C=C2I)I)I)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of potassium carbonate (3.0 g, 21.9 mmol, 1.1 eq), 3-iodophenol (4.4 g, 19.9 mmol) and 6-(2,4,6-triiodophenoxy)-1-chlorohexane (11.75 g, 19.9 mmol) in 50 ml of DMF was heated to 110° C. for 1.5 hours and then cooled. The mixture was poured into water and extracted with ethyl acetate. The organic layer was dried (magnesium sulfate) and evaporated to give a solid which was filtered through basic alumina (hexanes-ethyl acetate). The filtrate was concentrated under vacuum leaving the crude product as a solid. Recrystallization from cyclohexane afforded 8.29 g (54%) of the desired product after drying at room temperature under high vacuum, mp 65°-66° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:CC1=C(C(=O)O)C=C(C(=C1C)C)C, amount is: 0.0 ;m1_m4_m2_m3:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C(Cl)Cl, amount is: 0.0 ,Catalysts are m1_m4_m2_m3:CN(C=O)C, amount is: 0.0 .Products are 0:CC1=C(C(=O)Cl)C=C(C(=C1C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 3 L 3-necked flask is equipped with a condenser, argon inlet, thermowell, magnetic stirrer. The flask is purged with argon then charged with 2,3,4,5-tetramethylbenzoic acid (138.3 g, 0.776 mol), methylene chloride (1.5 L), thionyl chloride (73.5 mL, 1.01 mol) and N, N-dimethylformamide (2.0 mL, 0.026 mol). The resulting suspension is heated to reflux, after a clear solution is formed, heating is continued for 3.5 hours. The solution is allowed to cool then concentrated in vacuo. Last traces of thionyl chloride are removed by co-distillation with toluene (2×100 mL). The remaining oil is dried under high vacuum then used without further purification. Additional reactions are carded out to produce a total of 218 g of 2,3,4,5-tetramethylbenzoyl chloride. |
Here is a chemical reaction formula: Reactants are m1_m5:C(CC(=O)O)(=O)OCC, amount is: 0.0 ;m3:CC1=C(C(=O)Cl)C=C(C(=C1C)C)C, amount is: 0.0 ;m2:C(CCC)[Li], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ;m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C=C(C(=C1C)C)C)C(CC(=O)OCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 5 L, 3-necked flask is equipped with an overhead stirrer, addition funnel, thermowell and argon inlet. The flask is purged with argon then charged with ethyl hydrogen malonate (139.8 g, 1.06 mol) and tetrahydrofuran (2.3 L). The flask is cooled to -65° C. in a dry-ice/acetone bath. The n-butyllithium (892 mL, 2.23 mol) is transferred to the addition funnel then added dropwise to the stirred solution over a 2 hour period. After complete addition the reaction is warmed to -5° C. and stirred for 15 minutes. The resulting thick slurry is cooled to -65° C. The addition funnel is rinsed with tetrahydrofuran (20 mL) and the 2,3,4,5-tetramethylbenzoyl chloride (152.6 g, 0.776 mol) in tetrahydrofuran (250 mL) is transferred to the addition funnel under argon then added dropwise to the reaction over a 1.5 hour period. After complete addition the mixture is stirred at -65° C. for 1.5 hours. The reaction is allowed to warm to -20° C. then quenched over a water-ice mixture (3 L total volume). The solution is acidified to pH 2 by the slow addition of concentrated HCl. The product is extracted with ether (3×1 L), washed with saturated NaCO3 (2×1.5 L) and brine (1×1.5 L), dried over MgSO4, then concentrated in vacuo to a tan oil. An additional reaction is carried to produce a total of 185.1 g of crude product. Attempts to purify this material by vacuum distillation result in the apparent partial decomposition of the product. The remaining material is divided into two portions with each being chromatographed over 2 kg of silica eluted with methylene chloride. The TLC pure fractions are combined, concentrated in vacuo at 40° C. to constant weight, 108.5 g (42% yield). |
Here is a chemical reaction formula: Reactants are m2:COC1OC(CC1)OC, amount is: 0.0 ;m1:NC=1C=CC2=C(N=C(O2)C)C1, amount is: 0.0 ;m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:N1(C=CC=C1)C=1C=CC2=C(N=C(O2)C)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Amino-2-methylbenzoxazole (30.0 g, 0,203 mol) and 2,5-dimethoxytetrahydrofuran (30.0 g, 0.227 mol) were combined with 90 mL of acetic acid and the solution was heated at reflux for 1 hr. The mixture was evaporated to a red slurry and mixed with hexane to give a dark solid. The solid was dissolved in methylene chloride and extracted with basic water. The organic phase was removed, dried, and evaporated to a brown solid. Recrystallization from hexane/heptane afforded 18 g (45% yield) of product, m.p. 115°-121° C. |
Here is a chemical reaction formula: Reactants are m1:NC=1C=CC2=C(N=C(O2)C)C1, amount is: 0.0 ;m2:N(=O)OCCC(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:O1C=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O1C(=CC=C1)C=1C=CC2=C(N=C(O2)C)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Amino-2-methylbenzoxazole (7.0 g, 0.05 mole), isopentyl nitrite (20 mL), and furan (230 mL) were combined and heated with stirring at 30° C. in a roundbottom flask equipped with a condenser. After heating for 48 hrs, the reaction mixture was removed from the heat, washed with water, and then evaporated to an oil. Distillation afforded the product (4.0 g, 43% yield), bp 130°-140° C. (0.6 mm). Recrystallization from isopropyl alcohol (14 mL) afforded 3.0 g (32% yield), mp 60° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m5_m3:Cl.CC1=C(N)C=CC(=C1)N(CC)CC, amount is: 0.0 ;m1_m4_m2_m5_m3:C(=O)([O-])[O-].[Na+].[Na+], amount is: 0.0 ;m1_m4_m2_m5_m3:[O-]S(=O)S(=O)[O-].[Na+].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2_m5_m3:C(Cl)Cl, amount is: 0.0 ;m1_m4_m2_m5_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(N)C=CC(=C1)N(CC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-methyl-4-diethylaminoaniline hydrochloride (95.5 g, 460 mmol) in 200 mL of CH2Cl2 and Na2CO3 (21.6 g, 460 mmol) in 100 mL of water was stirred for 0.5 hr in the presence of a small amount of Na2S2O4 to prevent air oxidation. The layers were separated and the CH2Cl2 layer was dried over K2CO3, filtered and concentrated to afford free 2-methyl-4-diethylaminoaniline. 1,6-Diisocyanatohexane (75 g, 445 mmol) was taken up in 400 mL of THF. The tree phenylenediamine was dissolved in 100 mL of THF and added to the diisocyanatohexane solution via a dropping funnel. The mixture was stirred and then maintained at room temperature overnight. The mixture was filtered, and the filtrate was concentrated, and the remaining solid was washed with petroleum ether and filtered again to provide very pure product. The original precipitate collected was composed of the desired product and bis-protected product. This was taken up in 1 L of THF, refluxed for 15 minutes, then filtered. The filtrate was concentrated to provide a solid, washed with ether, and filtered to provide the desired product. The solid filtered-off after refluxing also contained some of the desired product, however, further isolation was not pursued. Overall yield was 63 g (40%). ##STR11## |
Here is a chemical reaction formula: Reactants are m1_m2:BrCCCCCCCCCC(CO)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:COC(C)(C)OC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[CH2-]C(=O)C.BrCCCCCCCCCC(CO)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 11-Bromoundecan-1,2-diol (2.65 g) was dissolved in 2,2-dimethoxypropane (10 mL) and acetone (20 mL) which had been dried over anhydrous K2CO3 for 1 hour. Toluene sulfonic acid (0.18 g) was added and the reaction stirred at room temperature for 19 hours. Solid K2CO3 was added and the mixture was stirred for 30 minutes. The solid was filtered off and the solvent evaporated. The product (11-bromoundecan-1,2-diol acetonide) was isolated in 79% yield (2.42 g) by flash chromatography on Sio2 with CH2Cl2. |
Here is a chemical reaction formula: Reactants are m1_m4:C(C1=CC=CC=C1)(=O)NN, amount is: 0.0 ;m3:Cl, amount is: 0.0 ;m2:S(=O)(=O)(C1=CC=C(C)C=C1)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N#N.S(=O)(=O)(C1=CC=C(C)C=C1)C1=C(C(=O)NN)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Benzhydrazide (4.08 g) was dissolved in pyridine (25 mL) and cooled on ice. Tosyl chloride (5.72 g) was added portionwise over 5 minutes. Stirring was maintained at 0° C. for 15 minutes. Stirring at room temperature for 18 hours was followed by pouring into dilute HCl (650 mL). The resultant precipitate was filtered off, washed with water, and recrystallized from hot ethanol/water to afford 6.76 g of product as fine white needles. |
Here is a chemical reaction formula: Reactants are m2:N(N)C(C(=O)O)(CC1=CC(=C(C=C1)O)OC)C, amount is: 0.0 MOLE;m1:NC(C(=O)O)(CC1=CC(=C(C=C1)O)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:NC(C(=O)OCCCC)(CC1=CC(=C(C=C1)O)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The procedure of Example 1 was repeated employing 2-amino-2-methyl-3-(3,4-dihydroxyphenyl)propionic acid rather than 2-hydrazino-2 -methyl-3-(4-hydroxy-3-methoxyphenyl)propionic acid. The butyl (±)-2-amino-2-methyl-3-(3,4-dihydroxyphenyl)propionate was obtained in a yield of 82%. The product was recrystallized from acetonitrile (77% yield) to give pure ester: mp 121.5 ° C. to 122.0° C.; HPLC analysis (C-18 column, 280 nm, tR =14.5 min) showed >99% purity. |
Here is a chemical reaction formula: Reactants are m1_m2:CCC(=O)C(CC(C)N(C)C)(C=1C=CC=CC1)C=2C=CC=CC2.Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CCC(=O)C(CC(C)N(C)C)(C=1C=CC=CC1)C=2C=CC=CC2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methadone (free base) was prepared for step B below by dissolving 10 grams of methadone hydrochloride in 100 mL of warm water at approximately 50° C. and crystallizing the free base out of solution by slowly adding 20 mL of a saturated aqueous potassium carbonate solution, pH 12.2 to the methadone hydrochloride solution with stirring. After crystallization was complete, the methadone crystals were filtered and redissolved in about 75 mL ethanol (ETOH). Following this the methadone was precipitated by the addition of 200 mL of water. The precipitate was filtered and dried in vacuo. The resulting yield of methadone was 8.79 g methadone or approximately 98%. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC1=C(C=CC=C1Cl)[N+](=O)[O-], amount is: 0.0 ;m1_m2:[F-].[K+], 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:ClC=1C(=C(C=CC1)[N+](=O)[O-])F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 57.6 g (0.3 mol) of 2,3-dichloronitrobenzene and 13.9 g (0.24 mol) of potassium fluoride were introduced into a 100 ml flange flask and fitted with a reflux condenser and blade stirrer and stirred at 150° C. for 2 hours (no reaction). The reaction suspension was heated to 190° C. and stirred for a further 4 hours at this temperature. Amount of 3-chloro-2-fluoronitrobenzene formed: after 2 hours: 1 GC area-%. after 8 hours: 8 GC area-%. |
Here is a chemical reaction formula: Reactants are m1_m2_m5:ClS(=O)(=O)N=C=O, amount is: 0.0 ;m1_m2_m5:NC1=NC(=CC(=N1)OC)OC, amount is: 0.0 ;m3_m4_m6:C1(CC1)C(=O)C1=C(C=CC(=C1)F)N, amount is: 0.0 ;m3_m4_m6:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:C(Cl)Cl, amount is: 0.0 MOLE;m3_m4_m6:C(Cl)Cl, amount is: 0.0 MOLE;m8:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1(CC1)C(=O)C1=C(C=CC(=C1)F)NS(=O)(=O)NC(=O)NC1=NC(=CC(=N1)OC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Chlorosulfonyl isocyanate (2.0 mL, 3.25 g, 23.0 mmol) is added to a solution of 2-amino-4,6-dimethoxypyrimidine (4.13 g, 26.6 mmol) in methylene chloride at 0° C. The resulting mixture is stirred for 30 minutes and a solution of 2-amino-5-fluorophenyl cyclopropyl ketone (4.77 g, 26.6 mmol) and triethylamine (6.3 mL, 4.57 g, 45.2 mmol) in methylene chloride is slowly added to the mixture. The resulting solution is stirred at room temperature for 18 hours, concentrated in vacuo and dissolved in methanol. The methanol solution is adjusted to about pH 1 with 10% hydrochloric acid and extracted with methylene chloride. The combined organic extracts are dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and 30% to 50% ethyl acetate in hexanes solutions affords a residue which is crystallized from an ether/petroleum ether solution to give the title product as a pale yellow solid (2.83 g, 24%, mp 76°-78° C.). |
Here is a chemical reaction formula: Reactants are m2:C(C)C(C(=O)O)CCCC, amount is: 0.0 ;m1:[OH-].[K+], amount is: 0.0 ;m3:[OH-].[K+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)C(C(=O)[O-])CCCC.[K+], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Potassium hydroxide (67.3 g) was suspended in tetrahydrofuran (1.2 liters) and to the suspension was added 2-ethylhexanoic acid (173.1 g) was added. The mixture was stirred until potassium hydroxide was dissolved to obtain a solution of potassium 2-ethylhexanoate. |
Here is a chemical reaction formula: Reactants are m1_m3:C(=O)(OC(C)(C)C)N[C@@H](CC(N)=O)C(=O)O, amount is: 0.0 ;m2_m4:C1(CCCCC1)N=C=NC1CCCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:N1=CC=CC=C1, amount is: 0.0 ;m2_m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)CC(C(=O)O)NC(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 20.0 g (86 mmol, 1 equiv.) of Boc-L-asparagine was dissolved in 120 mL of dry pyridine and 20.0 g (97 mmole, 1.3 equiv.) of dicyclohexylcarbodiimide dissolved in 60 mL of dry pyridine was added dropwwise over a period of 30 minutes. The reaction was stirred for 3 hours at 23° C. and filtered through a 2 μm nylon filter. The filtrate was concentrated in vacuo on a rotary evaporator and 100 mL of water was added. The pH was adjusted to 10 with 40% NaOH (aq.) and the solution filtered through a 2 μm nylon filter once again. The filtrate was passed through a 120 mL bed of Dowex 50X8-400 ion exchange resin and the resin washed with four column volumes of 1:1 methanol:water. The filtrate was concentrated in vacuo to yield 17.5 g (95% yield) of the title compound as a white solid. 1H-NMR (CD3OD): 4.40 p.p.m (m, 1H); 2.95 p.p.m. (m, 2H); 1.40 p.p.m. (s, 9H). |
Here is a chemical reaction formula: Reactants are m1_m3:C(#N)CC(C(=O)O)NC(=O)OC(C)(C)C, amount is: 0.0 ;m2:C(CCC)[Sn](CCCC)(CCCC)N=[N+]=[N-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1N=NN=C1CC(C(=O)O)NC(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 17.5 g (82 mmol, 1 equiv.) of the compound of Example 39 (3-cyano-2-(1,1-dimethylethoxy)methanamide-propionic acid) was dissolved in 125 mL of THF and 40.5 g (129 mmol, 1.5 equiv.) tributyltin azide was added. The reaction mixture was brought to reflux and held there for 3 days. The reaction mixture was cooled and the volatile removed in vacuo on the rotary evaporator. The residue was dissolved in 300 mL of 0.5M NaOH and this aqueous solution was washed with ethyl acetate (4×100 mL). The aqueous layer was passed through a 125 mL bed of Dowex 50X8-400 ion exchange resin and the resin washed with four column volumes of 1:1 methanol:water. The volatiles were removed in vacuo on the rotary evaporator to yield 17.9 g of the title compound as a white solid (85% yield). 1H-NMR (CD3OD): 4.55 p.p.m. (m, 1H); 3.40 p.p.m. (m, 2 H); 1.40 p.p.m. (s, 9H). This material is suitable for use in solid-phase peptide synthesis. |
Here is a chemical reaction formula: Reactants are m2:C(CCC)[Sn](CCCC)(CCCC)N=[N+]=[N-], amount is: 0.0 ;m1_m3:C(#N)CC(C(=O)OC)NC(=O)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1N=NN=C1CC(C(=O)OC)NC(=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2.5 g (9.54 mmol, 1 equiv.) of the compound of Example 51 (3-cyano-2-benzyloxymethanamidopropionic acid, methyl ester) was dissolved in 10 mL of dry THF and 3.0 g (9.54 mmol, 1 equiv.) of tri-n-butyltin azide was added. The reaction was refluxed for 72 hours followed by concentration in vacuo. 50 mL of 1M NaOH was added and the aqueous solution was extracted with ethyl acetate (3×50 mL). The aqueous solution was acidified to pH=1 with 4M HCl and extracted with ethyl acetate (4×60 mL). After drying over sodium sulfate, the organics were decanted and concentrated in vacuo to yield 2.5 g of the title compound. 1H-NMR (CDCl3): 7.3 p.p.m. (m, 5H); 6.1 p.p.m. (m, 1H); 5.1 p.p.m. (s, 2H); 4.8 p.p.m. (m, 1H); 3.8 p.p.m. (s, 3H); 3.5 p.p.m. (m, 2H). |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 ;m1_m3:N1N=NN=C1CC(C(=O)OC)NC(=O)OCC1=CC=CC=C1, 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:Cl.N1N=NN=C1CC(C(=O)OC)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.53 g (1.74 mmol, 1 equiv.) of the compound of Example 52 (3-tetrazolyl-2-benzyloxymethanamidopropionic acid, methyl ester) was dissolved in 30 mL of methanol and 1 mL of conc. HCl was added. The reaction was flushed with nitrogen and 80 mg of 10% palladium on carbon was added. The solution was hydrogenated for 2 hours at 40 psi. Filtration of the catalyst followed by counteraction in vacuo yielded 354 mg of the title compound. 1H-NMR (CD3OD): 4.7 p.p.m. (m, 1H); 3.8 p.p.m. (s, 3H); 3.6 p.p.m. (m, 2H). |
Here is a chemical reaction formula: Reactants are m1:NC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H](O)[C@H](O)[C@H](O1)CO)OC, amount is: 0.0 ;m2_m3:O, amount is: 0.0 ;m2_m3:C(CC)(=O)OCC(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H](O)[C@H](O)[C@H](O1)COC(CC)=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Amino-6-methoxy-9-(β-D-arabinofuranosyl)-9H-purine (1.0 g, 3.3 mmol) (prepared as described in European Patent Application No. 294 114) was suspended in 40 ml of pyridine that contained 300 μL of H2O and 2 ml of trichloroethyl propionate (Trichloroethyl propionate was synthesized by addition of 19 ml of propionyl chloride (Aldrich) over 30 minutes to 19.1 ml of trichlorethanol (Aldrich) in 40 ml of pyridine at 0° C.). The product was purified by successive washing with 2×100 ml aliquots of H2O, 5% NaHCO3, and H2O. 1H NMR (200 MHz, CDCl3, 4.74 (s, 2H, Cl3CH2-), 2.49 (q, 2H, J=7.6 Hz, CH3CH2CO2-), 1.21 (t, 3H, J-7.6 Hz, CH3CH2CO2-). The reaction was initiated with 0.100 g of subtilisin (Sigma Chemical Co., St. Louis, Mo., P-5380, lot No. 38F-0356), whch had been activated by dissolving 1 g of the enzyme in 20 ml of 0.1M potassium phosphate at pH 7.8 and lyophilizing to dryness. After stirring for 23 hours at 40° C., the reaction was quenched by filtering off the enzyme and the solvent was removed in vacuo. The crude product was purified by chromatography on a 4.5×25 cm silica gel column with CH2Cl2 :CH3OH (9:1) as eluant. Product fractions were pooled and lyophilized from water to yield 0.76 g of the desired product as a white powder: m.p. 124° C.; TLC Rf =0.43 (silica gel; CH2Cl2 :CH3OH (9:1); UV λmax (ε, mM-1 cm-1) at pH 7.0, 2.78 nm (9.5). |
Here is a chemical reaction formula: Reactants are m4:[OH-].[Na+], amount is: 0.0 ;m1_m2_m3:CC(=O)N1CCN(CC1)CC2=C(C(=C(C=C2)OC)OC)OC, amount is: 0.0 ;m1_m2_m3:C(C)OCC, amount is: 0.0 ;m1_m2_m3:[H-].[H-].[H-].[H-].[Li+].[Al+3], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ;m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)N1CCN(CC1)CC1=C(C(=C(C=C1)OC)OC)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: ##STR6## 30.8 g (0.1 mol) of N-acetyltrimetazidine, 600 ml of diethyl ether and 11.1 g (0.3 mol) of LiAlH4 are heated to and then maintained at reflux for 24 hours with vigorous stirring, the mixture is subsequently allowed to return to room temperature, and stirring is continued for a further 12 hours, after which the mixture is hydrolysed in succession with 10 ml of water, 10 ml of 4N sodium hydroxide solution and finally 30 ml of water. The mixture is filtered and the residue is washed three times with 200 ml of diethyl ether each time. The ethereal phases are removed and the residue is then taken up three times with 300 ml of CH2C2 each time. The organic phase obtained after filtration is dried over magnesium sulphate, and the solvent is then removed by evaporation in vacuo. The residue (approximately 20 g) is filtered over 150 g of silica using a mixture of chloroform and ethanol (97.5% -2.5%) as eluants. 18 g of N-ethyl-N'-(2-hydroxy-3,4-dimethoxybenzyl)-piperazine are obtained directly (yield: 64%). |
Here is a chemical reaction formula: Reactants are m1_m2:C(C1=CC=CC=C1)N1CCN(CC1)CC1=C(C(=C(C=C1)OC)OC)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)O, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:OC1=C(CN2CCNCC2)C=CC(=C1OC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: ##STR7## 6.8 g (0.02 mol) of N-benzyl-N'-(2-hydroxy-3,4-dimethoxy-benzyl)-piperazine are dissolved in 200 ml of ethanol at 60° C. 1.1 g of 5% palladium on carbon are added thereto and the whole is hydrogenated under a pressure of 5,500 hPa, after which the alcoholic solution is filtered and the solvent is distilled off. The oil obtained is chromatographed on 150 g of silica. A first elution with dichloromethane removes the lower polarity impurities from the mixture. The silica is then washed with a CH2C2 /CH3OH mixture (90/10). 3.78 g of N-(2-hydroxy-3,4-dimethoxybenzyl)-piperazine are obtained (60% yield), and the compound is then converted into its dihydrochloride (m.p. >190° C.) by adding twice the stoichiometric amount of HCl. |
Here is a chemical reaction formula: Reactants are m1_m5:C(C)S(=O)(=O)N, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 ;m3:ClC1=NC=C(C=C1[N+](=O)[O-])C(F)(F)F, 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:[N+](=O)([O-])C=1C(=NC=C(C1)C(F)(F)F)NS(=O)(=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3.1 g of ethanesulfonamide was dissolved in 50 ml of dry tetrahydrofuran, and 1.2 g of 60% sodium hydride was added thereto under cooling with ice. After completion of the addition, the mixture was reacted for one hour under reflux. After cooling, 5.0 g of 2-chloro-3-nitro-5-trifluoromethylpyridine was added thereto, and then the mixture was reacted for 7 hours under reflux. After completion of the reaction, the reaction product was poured into 200 ml of water. Undissolved materials in water were extracted with ethyl ether and removed. Then, the aqueous layer was weakly acidified with dilute hydrochloric acid. Precipitated crystals were collected by filtration and dried to obtain 3.6 g of N-(3-nitro-5-trifluoromethyl-2-pyridyl)ethanesulfonamide having a melting point of from 160° to 163° C. |
Here is a chemical reaction formula: Reactants are m3:[H-].[Na+], amount is: 0.0 ;m1:CS(=O)(=O)NC1=NC=C(C=C1NC(C1=CC=C(C=C1)F)=O)C(F)(F)F, amount is: 0.0 MOLE;m2_m5:CS(=O)(=O)N, amount is: 0.0 ;m4:ClC1=NC=C(C=C1[N+](=O)[O-])C(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m2_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C=1C(=NC=C(C1)C(F)(F)F)NS(=O)(=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Preparation of N-(2-methylsulfonylamino-5-trifluoromethyl-3-pyridyl)-4-fluorobenzamide (Compound No. 10) (1) 4.4 g of methanesulfonamide was dissolved in 70 ml of dry tetrahydrofuran, and 1.9 g of 60% sodium hydride was added thereto under cooling with ice. After completion of the addition, the mixture was reacted for one hour under reflux. After cooling, 7.0 g of 2-chloro-3-nitro-5-trifluoromethylpyridine was added thereto, and the mixture was reacted for 6 hours under reflux. After completion of the reaction, the reaction product was poured into 300 ml of water and washed with ethyl ether. Then, the aqueous layer was weakly acidified with dilute hydrochloric acid. Precipitated crystals were collected by filtration and dried to obtain 5.8 g of N-(3-nitro-5-trifluoromethyl-2-pyridyl)methanesulfonamide having a melting point of from 138° to 139° C. |
Here is a chemical reaction formula: Reactants are m2:ClC(C(=O)Cl)(Cl)Cl, amount is: 0.0 ;m4_m1:NC1=NC=C(C=C1N)C(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:O1CCCC1, amount is: 0.0 ;m4_m1:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=NC=C(C=C1NC(C(Cl)(Cl)Cl)=O)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Into 38 ml of dry tetrahydrofuran, 1.5 g of 2,3-diamino-5-trifluoromethylpyridine was dissolved, and a solution mixture comprising 1.54 g of trichloroacetyl chloride and 3.8 ml of dry tetrahydrofuran was dropwise added thereto over a period of 10 minutes. Then, the mixture was reacted at room temperature for 3 hours. After completion of the reaction, precipitated crystals were collected by filtration and washed with tetrahydrofuran to obtain 2.2 g of N-(2-amino-5-trifluoromethyl-3-pyridyl)trichloroacetamide having a melting point of from 210° to 223° C. |
Here is a chemical reaction formula: Reactants are m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m4:O, amount is: 0.0 ;m1_m2_m5:C(C)S(=O)(=O)N, amount is: 0.0 ;m1_m2_m5:ClC1=NC=C(C=C1)C(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:CS(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C=1C=CC(=NC1)NS(=O)(=O)CC)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 20.3 g of ethanesulfonamide and 26.0 g of 2-chloro-5-trifluoromethylpyridine were dissolved in 220 ml of dimethylsulfoxide, and 47.4 g of anhydrous potassium carbonate was further added thereto. This solution mixture was heated to 130° C. and reacted for 5 hours. After completion of the reaction, the reaction product was poured into 1 l of water. Undissolved materials in water were extracted with ethyl ether and removed. Then, the aqueous layer was adjusted to pH4 with concentrated hydrochloric acid, and precipitated crystals were collected by filtration and dried to obtain 26.2 g of N-(5-trifluoromethyl-2-pyridyl)ethanesulfonamide having a melting point of from 164° to 165° C. |
Here is a chemical reaction formula: Reactants are m2_m5:[N+](=O)([O-])C=1C(=NC=C(C1)C(F)(F)F)NS(=O)(=O)CC, amount is: 0.0 ;m3:[Cl-].[Na+], amount is: 0.0 MOLE;m1_m4:S(=O)([O-])S(=O)[O-].[Na+].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:O1CCCC1, amount is: 0.0 ;m6:O1CCCC1, amount is: 0.0 MOLE;m1_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC=1C(=NC=C(C1)C(F)(F)F)NS(=O)(=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: An alternative process will be described. To a solution prepared by dissolving 34.9 g of sodium hydrosulfite in 400 ml of water, a solution prepared by dissolving 5.0 g of N-(3-nitro-5-trifluoromethyl-2-pyridyl)ethanesulfonamide in 80 ml of tetrahydrofuran, was dropwise added at room temperature. After completion of the dropwise addition, the mixture was reacted for further 3 hours. After completion of the reaction, sodium chloride was added until the tetrahydrofuran layer was separated. The separated tetrahydrofuran layer was dried, and tetrahydrofuran was distilled off under reduced pressure to obtain 4.2 g of N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamide. |
Here is a chemical reaction formula: Reactants are m2:C1(CCCCC1)C(=O)Cl, amount is: 0.0 ;m1_m3:NC=1C(=NC=C(C1)C(F)(F)F)NS(=O)(=O)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)S(=O)(=O)NC1=NC=C(C=C1NC(=O)C1CCCCC1)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2.36 g of N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamide was dissolved in 24 ml of dry tetrahydrofuran, and 1.54 g of cyclohexanecarbonyl chloride was dropwise added thereto under cooing with ice. After the dropwise addition, the mixture was stirred for one hour and further reacted at room temperature overnight. After completion of the reaction, the solvent was distilled off under reduced pressure, the obtained crystals were washed with ethyl ether to obtain 2.94 g of the desired product having a melting point of from 153° to 155° C. |
Here is a chemical reaction formula: Reactants are m1:Cl.C(C)N=C=NCCCN(C)C, amount is: 0.0 ;m2:NC=1C(=NC=C(C1)C(F)(F)F)NS(=O)(=O)CC, amount is: 0.0 ;m3:C1(CCCCC1)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(Cl)Cl, amount is: 0.0 ;m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)S(=O)(=O)NC1=NC=C(C=C1NC(=O)C1CCCCC1)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: An alternative process will be described. In 20 ml of methylene chloride, 0.5 g of 4-diemthylaminopyridine was dissolved, and 0.78 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added and dissolved. Then, 1 g of N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamide was added thereto, and 30 minutes later, 0.52 g of cyclohexanecarboxylic acid was added thereto, and stirring was conducted for 10 hours. After completion of the reaction, 40 ml of methylene chloride was added to the reaction product, and the reaction product was washed with 10% hydrochloric acid and then washed with an aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. From the extract layer, solvent was distilled off and the obtained residue was purified by silica gel column chromatography to obtain 0.88 g of the desired product. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:C(\C=C\C)=O, amount is: 0.0 ;m1_m3_m2_m4:C1(CC(CCC1)=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:N1=CC=CC=C1, amount is: 0.0 ;m1_m3_m2_m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1OC2=C(C=C1)C(CCC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of crotonaldehyde (72.74 g, 1.04 mol) in 500 mL of pyridine was added to 1,3-cyclohexanedione (100 g, 0.892 mol) in 500 mL of pyridine and the mixture was heated to reflux under a nitrogen atmosphere for 1 hour. The mixture was cooled to room temperature and then filtered through magnesium sulfate (328 g). The filtrate was concentrated to dryness and the residue was partitioned between water and diethyl ether. The aqueous phase was extracted with diethyl ether and the combined diethyl ether layers were washed with 10% hydrochloric acid (3×150 mL). The diethyl ether layer was then washed with water to neutrality, dried (MgSO4), filtered and the filtrate concentrated to dryness. The residue was purified by Kugelrohr distillation (bp 109°-112° C. (1 to 2 mm)) to give 2-methyl-5,6,7,8-tetrahydro-2H-1-benzopyran-5-one (48.2 g, 0.294 mol) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC=1C=CC2=C(NC(C(=CC2=O)OC)=O)C1, amount is: 0.0 ;m1_m3_m2:N, 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:NC1=CC(C2=C(NC1=O)C=C(C=C2)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 8-Chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.4 g) was treated with 80 mL of liquid anhydrous ammonia chilled to -78 ° C. The mixture was sealed in a pressure vessel and warmed to 26° C. for 22.5 hours. The excess ammonia was evaporated to give a solid. The solid was recrystallized from 5 mL hot dimethylformamide and water; crystallization was initiated by cooling the solution in an ice bath. The solid was filtered, washed (water) and vacuum dried (100 ° C., 15 Pa) to give the title compound (0.274 g); mp 44.5-346.4 ° C. (dec); NMR: 11.47 (s,1), 8.10 (d,1, J=8.7), 7.53 (d,1, J=2.0), 7.27 (dd,1, 3=8.7, 2.0), 7.1 (broad s,2, NH2), 6.23 (s,1). Analysis for C10H7ClN2O2 : Calculated: C, 53.95; H, 3.17 ; N, 12.58; Found: C, 53.80; H, 3.34; N, 12.89. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC=1C=CC2=C(NC(C(=CC2=O)OC)=O)C1, amount is: 0.0 ;m1_m2:C(CC1=CC=CC=C1)N, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC=1C=CC2=C(NC(C(=CC2=O)NCCC2=CC=CC=C2)=O)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 8-Chloro-3-methoxy-2,5-dioxo-2,5-dihydro1H-benz[b]azepine (0.5 g) was treated with 5 mL of phenethylamine, and the mixture was heated to 80° C. for 1 hour. The reaction mixture was filtered and the solid recrystallized from 5 mL hot dimethylformamide and water. The solid was filtered, washed (water) and vacuum dried (100° C., 15 Pa) to give the title compound (0.329 g); mp 284.4-286.9° C.; NMR: 5.89 (s,1): MS: m/z=327(M+1). Analysis for C18H15ClN2O2 ·0.2 H2O: Calculated: C, 65.44; H, 4.70; N, 8.48; Found: C, 65.42; H, 4.72; N, 8.62. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC=1C=CC2=C(NC(C(=CC2=O)OC)=O)C1, amount is: 0.0 ;m1_m3_m2:C(C1=CC=CC=C1)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)NC1=CC(C2=C(NC1=O)C=C(C=C2)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.5 g) in methanol (15 mL) was added benzylamine (0.3 mL). The mixture was heated to reflux for 24 hours. The solvent was evaporated to give a solid. The solid was recrystallized from dimethylformamide (5 mL) and water, washed (water) and vacuum dried (100° C., 15 Pa) to give the title compound (0.181 g); mp 309.1°-313.9° C.; NMR: 5.73 (s,1); MS: m/z=313(M+1). Analysis for C17H13ClN2O2 : Calculated: C, 65.29; H, 4.19; N, 8.96; Found: C, 65.02; H, 3.96; N, 8.61. |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 MOLE;m1_m2:COC1=CC(C2=C(NC1=O)C=CC=C2)=O, amount is: 0.0 ;m1_m2:NC1=CC=CC=C1, 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:N(C1=CC=CC=C1)C1=CC(C2=C(NC1=O)C=CC=C2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-Methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (1.0 g) and aniline (10 mL) were heated to reflux for 5 hours and diluted with water. Hydrochloric acid (2N) was added and the mixture extracted with ethyl acetate. The organic extracts were washed (acid, brine), dried and evaporated to give a solid which was purified by chromatography, with ethyl acetate:toluene (1:4) as the eluent. Recrystallization from ethyl acetate gave the title compound (0.405 g); mp 227°-228° C.: NMR: 6.28 (s,1); MS(E1): m/z=264(M). Analysis for C16H12N2O2 ·0.1 H2O: Calculated: C, 72.22; H, 4.62; N, 10.53; Found: C, 72.32; H, 4.68; N, 10.65. |
Here is a chemical reaction formula: Reactants are m1_m2:COC1=CC(C2=C(NC1=O)C=CC=C2)=O, amount is: 0.0 ;m1_m2:N(CCO)CCO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:OCCN(CCO)C1=CC(C2=C(NC1=O)C=CC=C2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-Methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (1.0 g) was treated with diethanolamine (10 mL), and the mixture was heated to 140° C. for 2 hours. The mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and evaporated. The solid was recrystalized from ethanol to give the title compound (53 mg); mp 204°-205° C.; NMR: 5.90 (s,1); MS: m/z=277(+1). Analysis for C14H16NO4 : Calculated: C, 60.80; H, 5.84; N, 10.14; Found: C, 61.29; H, 5.29; N, 11.74. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC1=CC(C2=C(NC1=O)C=CC=C2)=O, amount is: 0.0 ;m1_m3_m2:C(O)CN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OCCNC1=CC(C2=C(NC1=O)C=CC=C2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (1.0 g) in methanol (20 mL) was added ethanolamine (0.36 g). The mixture was heated to reflux until a precipitate formed. The reaction mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from ethanol to give the title compound (0.72 g); mp 207° C.; NMR: 5.91 (s,1); MS(EI): m/z=232(M). Analysis for C12H12N2O3 ·0.2 H2O: Calculated: C, 61.11; H, 5.30; N, 11.88; Found: C, 61.13; H, 5.20; N, 11.72. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC1=C(C(C2=C(NC1=O)C=CC=C2)=O)C, 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:ClCCl, amount is: 0.0 MOLE;m4:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:OC1=C(C(C2=C(NC1=O)C=CC=C2)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-methoxy-4-methyl-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.47 g) in dichloromethane was added boron tribromide (6.5 mL). The precipitate which formed was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and evaporated. The solid was recrystallized from hot toluene to give the title compound (0.31 g); mp 252.3° C.; NMR: 2.07 (s,3); MS(EI): m/z=203(M). Analysis for C11H9NO3 ·0.2 H2O: Calculated: C, 63.89; H, 4.58; N, 6.77; Found: C, 63.79; H, 4.49; N, 6.73. |
Here is a chemical reaction formula: Reactants are m2:C(C)(=O)[O-].[Na+], amount is: 0.0 ;m1_m4:ClC=1C=CC2=C(NC(C(=CC2=O)OC)=O)C1, amount is: 0.0 ;m3:ICl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=CC2=C(NC(C(=C(C2=O)I)OC)=O)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (3.00 g) in glacial acetic acid (250 mL) was added sodium acetate (2.07 g) followed by iodine monochloride (15.2 mL). The mixture was heated to reflux for 1.5 hours, was allowed to cool, and the acetic acid was evaporated from the reaction mixture. The solid residue was suspended in tetrahydrofuran and stirred for 15 minutes. The solution was filtered and the resulting liltrate evaporated. The yellowish solid was recrystallized from refluxing toluene (700 mL) to afford the title compound (3.8 g); 250 MHz NMR: 11.60 (broad s, 1), 7.59 (d,1, J=7.1), 7.30 (d,1, J=1.4), 7.23 (dd,1, J=7.1, 1.6), 3.90 (s,3). Analysis for C11H7ClINO3 : Calculated: C, 36.34; H, 1.94; N, 3.85; Found: C, 36.35, H, 1.87; N, 3.82. |
Here is a chemical reaction formula: Reactants are m3:[F-].[K+], amount is: 0.0 ;m6_m2:C[Sn](C)(C)C, amount is: 0.0 ;m1:ClC=1C=CC2=C(NC(C(=C(C2=O)I)OC)=O)C1, amount is: 0.0 ;m4:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C1(=CC=CC=C1)C, amount is: 0.0 ,Catalysts are m6_m2:[CH2-]C1=CC=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd+], amount is: 0.0 .Products are 0:ClC=1C=CC2=C(NC(C(=C(C2=O)C)O)=O)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 8-Chloro-4-iodo-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.50 g) was suspended in toluene (12 mL) and trans-benzyl(chloro)bis(triphenylphosphine)palladium(II) (50 mg) and tetramethyltin (0.30 mL) were added. The mixture was allowed to reflux for 17 hours, was cooled to room temperature, and 10% (w/w) aqueous potassium fluoride (3 mL) was added, followed by 3N hydrochloric acid (10 mL). The resulting mixture was warmed to 50 ° C. for 6 hours. The reaction mixture was filtered, and the crude product was washed (water, hexane). Crystallization, twice, from dimethylformamide and water gave the title compound as an off-white solid (110 mg); mp 277°-279 ° C.; NMR: 11.72 (s,1), 10.28 (s,1), 7.95 (d,1, J=8.7), 7.48 (t,1, J=2.0), 7.31 (dd,1, J=8.7, 2.0), 2.07 (s,1). Analysis for C11H8ClNO3 ·0.10 H2 0: Calculated: C, 55.18; H, 3.45; N, 5.85; Found: C, 55.23; H, 3.47; N, 5.83. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC=1C=CC2=C(NC(C(=C(C2=O)I)OC)=O)C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)NCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=CC2=C(NC(C(=CC2=O)N(CC)CC)=O)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 8-Chloro-4-iodo-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.4 g) was treated with diethylamine (20 mL). The mixture was sealed in a pressure vessel and heated to 60° C. for 17 hours. The reaction mixture was concentrated to a brown solid which was recrystallized from hot ethyl acetate. The solid was filtered, washed and air dried to give the title compound as a yellow solid; NMR: 5.70 (s,1); MS: m/z=279(M+1). |
Here is a chemical reaction formula: Reactants are m3:C(C)(C)NC(C)C, amount is: 0.0 ;m5:CI, amount is: 0.0 ;m1_m2_m8:COC1=CC(C2=C(NC1=O)C=CC=C2)=O, amount is: 0.0 ;m1_m2_m8:[Cl-].[Li+], amount is: 0.0 ;m4:C(CCC)[Li], amount is: 0.0 ;m6:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m8:O1CCCC1, amount is: 0.0 ;m7:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC1=C(C(C2=C(NC1=O)C=CC=C2)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-Methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.5 g) and anhydrous lithium chloride (0.63 g) were added to dry tetrahydrofuran (10 mL), and the mixture was cooled to -70° C. To this was added diisopropylamine (380 mL), followed by butyllithium (2.2 mL, 2.5 M in hexanes); and the mixture was warmed to -20° C. After 30 minutes, methyl iodide (307 mL) was added and the mixture cooled to -10° C. for 10 minutes. The mixture was diluted with water, acidified with 2 N hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and evaporated. The solid was purified by chromatography, with ethyl acetate:toluene (1:1) as the eluent, and recrystallized from hot toluene to give the methylated product as a white solid (0.367 g); NHR: 2.03 (s,3); MS(EI): m/z=217(M). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C1(=CC=CC=C1)N=C=O, amount is: 0.0 ;m1_m2_m3_m4:NC1CCN(CC1)CC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CCC(CC1)NC(=O)NC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.14 ml (10.5 mmol) of phenyl isocyanate are slowly added dropwise to a solution of 1.90 g (10.0 mmol) of 4-amino-1-benzylpiperidine and 1.46 ml (10.5 mmol) of triethylamine in 40 ml of dichloromethane. The reaction mixture may subsequently be stirred at room temperature for 1 h, and is then evaporated to dryness in vacuo. The residue is mixed with 50 ml of diethyl ether, stirred well, separated off by filtration, washed with 5 ml of diethyl ether and dried in a high vacuum. 2.62 g (85%) of the title compound are obtained as colourless crystals. |