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Here is a chemical reaction formula: Reactants are m3:OS(=O)(=O)O, amount is: 0.0 ;m1_m2:BrC=1C=C(C=CC1)CCCC(C)(O)C, amount is: 0.0 ;m1_m2:BrC=1C=C(C=CC1)CCCC(C)(O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=C2CCCC(C2=CC1)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 15.0 g (58.3 mmol) of 5-(3-bromophenyl)-2-methyl-pentan-2-ol (Compound E) was cooled to 0° C. and then 2.8 ml of conc. H2SO4 was added. The mixture was stirred for 2.5 hours, diluted with water (20 ml) and extracted with Et2O (3×40 ml). The combined organic layers were washed with water, sat. aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. Purification by kugelrohr distillation gave the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are m6_m1_m2_m3_m4_m5:C(C)(=O)OC(C)=O, amount is: 0.0 ;m6_m1_m2_m3_m4_m5:C(C)(=O)O, amount is: 0.0 ;m6_m1_m2_m3_m4_m5:BrC=1C=C2CCCC(C2=CC1)(C)C, amount is: 0.0 ;m6_m1_m2_m3_m4_m5:BrC=1C=C2CCCC(C2=CC1)(C)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6_m1_m2_m3_m4_m5:C1=CC=CC=C1, amount is: 0.0 ,Catalysts are m6_m1_m2_m3_m4_m5:[O-2].[O-2].[O-2].[Cr+6], amount is: 0.0 .Products are 0:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a cold mixture (0° C.) of 209 g (200 mmol) of chromium trioxide, 100 ml (1.06 mol) of acetic anhydride and 200 ml (3.5 mol) of acetic acid was added a solution of 10 g (41.8 mmol) of 6-bromo-1,2,3,4-tet-rahydro-1,1-dimethylnaphthalene (Compound F) in 125 ml of benzene. The reaction mixture was stirred for 1 hour, quenched with ice cold water and extracted with Et2O (3×100 ml). The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (silica, 10% EtOAc-hexane) to give the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:BrC=1C=C2CCCC(C2=CC1)(C)C, amount is: 0.0 ;m1_m2_m5_m3:BrC=1C=C2CCCC(C2=CC1)(C)C, amount is: 0.0 MOLE;m1_m2_m5_m3:BrN1C(CCC1=O)=O, amount is: 0.0 ;m4:C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5_m3:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC1CCC(C2=CC=C(C=C12)Br)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1.2 g (5.0 mmol) of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound F) in 20 ml of CCl4 was added 0.97 g (5.5 mmol) of N-bromosuccinimide followed by 20 mg (0.08 mmol ) of benzoylperoxide. The mixture was refluxed for 3 hours, filtered and the filtrate washed with water (5 ml). The organic phase was dried over MgSO4 and then concentrated in vacuo to yield the title compound as a pale yellow oil. |
Here is a chemical reaction formula: Reactants are m6_m1:[Na], amount is: 0.0 ;m6_m1:C1(CCCCC1)O, amount is: 0.0 ;m3_m4_m5:BrC1CCC(C2=CC=C(C=C12)Br)(C)C, amount is: 0.0 ;m3_m4_m5:BrC1CCC(C2=CC=C(C=C12)Br)(C)C, amount is: 0.0 MOLE;m3_m4_m5:C1(CCCCC1)O, amount is: 0.0 ;m2:[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:BrC=1C=C2C(CCC(C2=CC1)(C)C)OC1CCCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 9 g (89.9 mmol) of cyclohexanol was added 160 mg (7.0 mmol) of sodium metal and the mixture was stirred at 70° C. for 12 hours. After all of the sodium dissolved the reaction mixture was cooled to ambient temperature and then a solution of 1 g (3.2 mmol) of 4,6-dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Compound I) in 1 ml of cyclohexanol was added. The mixture was heated at 120° C. for 4 hours and thereafter the excess solvent distilled off under reduced pressure. The product was dissolved in Et2O (75 ml), washed with water (5 ml) and brine (5 ml), dried over MgSO4 and concentrated in vacuo. Purification by column chromatography (silica, 5% EtOAc-hexane) yielded the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C, amount is: 0.0 MOLE;m1_m2_m3_m4:C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C, amount is: 0.0 MOLE;m1_m2_m3_m4:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C, amount is: 0.0 ;m1_m2_m3_m4:BrC1=CC=C2C(CCC(C2=C1)=O)(C)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:C(#C)C1=CC=C2C(CCC(C2=C1)=O)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of 6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound K), 7 g (27.6 mmol) of 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G) was converted into the title compound using 39 ml (36.6 mmol) of trimethylsilyl acetylene, 0.97 g (1.3 mmol) of bis(triphenylphosphine)palladium(II) chloride, 0.26 g (1.3 mmol) of cuprous iodide and 0.6 g (4.3 mmol) of K2CO3. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C, amount is: 0.0 MOLE;m1_m2_m3:C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C, amount is: 0.0 MOLE;m1_m2_m3:BrC1=CC=C2CCCC(C2=C1)(C)C, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(#C)C1=CC=C2CCCC(C2=C1)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of 6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound K), 2.1 g (8.8 mmol) of 7-bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene was converted into the title compound using 10 ml (93.9 mmol) of trimethylsilyl acetylene, 1.25 g (1.8 mmol) of bis(triphenylphosphine)palladium(II) chloride, 0.53 g (2.8 mmol) of cuprous iodide and 10 ml (20.0 mmol) of K2CO3 (2M solution in methanol). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C, amount is: 0.0 MOLE;m1_m2_m3_m4:C(#C)C=1C=C2C(CCC(C2=CC1)=O)(C)C, amount is: 0.0 MOLE;m1_m2_m3_m4:BrC=1C=C2C(CCC(C2=CC1)(C)C)OC1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4:BrC=1C=C2C(CCC(C2=CC1)(C)C)OC1CCCCC1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C1(CCCCC1)OC1CCC(C2=CC=C(C=C12)C#C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of 6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound K), 2.1 g (8.8 mmol) of 6-bromo-4-cyclohexyloxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Compound J) was converted into the title compound using 1 g (10.2 mmol) of trimethylsilyl acetylene, 0.14 g (0.20 mmol) of bis(triphenylphosphine)palladium(II) chloride, 19 mg (0.1 mmol) of cuprous iodide and 80 mg (0.6 mmol) of K2CO3. |
Here is a chemical reaction formula: Reactants are m5:BrN1C(CCC1=O)=O, amount is: 0.0 ;m1:C1=CC=CC2=CC=CC=C12.BrC=1C=C2CCCC(C2=CC1)(C)C, amount is: 0.0 MOLE;m6:C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O, amount is: 0.0 ;m2:C1=CC=CC2=CC=CC=C12.BrC=1C=C2CCCC(C2=CC1)(C)C, amount is: 0.0 MOLE;m3:BrC1=C(C2=CC=CC=C2C=C1)Br, amount is: 0.0 MOLE;m4:C1=CC=CC2=CC=CC=C12.BrC=1C=C2CCCC(C2=CC1)(C)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:BrC1CCC(C2=CC=C(C=C12)Br)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the above-described procedure for the conversion of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene (Compound F) to the dibromonaphthalene derivative (Compond I), 3.5 g (14.6 mmol) of (Compound F), 2.86 g (16.1 mmol) of N-bromosuccinimide and 150 mg (0.62 mmol ) of benzoylperoxide gave crude 4,6-dibromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound I). To a solution of this crude dibromonaphthalene derivative (Compound I) in 50 ml of THF was added 5.38 g (47.1 mmol) of potassium thioacetate. The mixture was refluxed for 6 hours under argon atmosphere, filtered through celite and concentrated in vacuo. Purification by chromatography (silica, 10% EtOAc-hexane) yielded the title compound as red oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:BrC1CCC(C2=CC=C(C=C12)Br)(C)C, amount is: 0.0 MOLE;m1_m2_m4_m3:BrC1CCC(C2=CC=C(C=C12)Br)(C)C, amount is: 0.0 MOLE;m1_m2_m4_m3:C(C)(=S)[O-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=C2C(CCC(C2=CC1)(C)C)C(C)=S, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the above-described procedure for the conversion of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene (Compound F) to the dibromonaphthalene derivative (Compond I), 3.5 g (14.6 mmol) of (Compound F), 2.86 g (16.1 mmol) of N-bromosuccinimide and 150 mg (0.62 mmol ) of benzoylperoxide gave crude 4,6-dibromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound I). To a solution of this crude dibromonaphthalene derivative (Compound I) in 50 ml of THF was added 5.38 g (47.1 mmol) of potassium thioacetate. The mixture was refluxed for 6 hours under argon atmosphere, filtered through celite and concentrated in vacuo. Purification by chromatography (silica, 10% EtOAc-hexane) yielded the title compound as red oil. |
Here is a chemical reaction formula: Reactants are m2:S(=O)(Cl)Cl, amount is: 0.0 ;m1_m3:IC1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)OC(C1=CC=C(C=C1)I)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 10 g (40.32 mmol) of 4-iodobenzoic acid in 100 ml absolute ethanol was added 2 ml thionyl chloride and the mixture was then heated at reflux for 3 hours. Solvent was removed in vacuo and the residue was dissolved in 100 ml ether. The ether solution was washed with saturated NaHCO3 and saturated NaCl solutions and dried (MgSO4). Solvent was then removed in vacuo and the residue kugelrohr distilled (100 degrees C.; 0.55 mm) to give the title compound as a colorless oil, PMR (CDCl3): δ1.42 (3H, t, J~7 Hz), 4.4 (2H, q, J~7 Hz), 7.8 (4H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5:ClC1=NC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m2_m3_m4_m5:C(C)O, amount is: 0.0 ;m1_m2_m3_m4_m5:C1(CCCCC1)N=C=NC1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4_m5:CN(C)C1=NC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=NC=C(C(=O)OCC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 15.75 g (0.1 mol) 6-chloronicotinic acid, 6.9 g (0.15 mol) ethanol, 22.7 g (0.11 mol) dicyclohexylcarbodiimide and 3.7 g dimethylaminopyridine in 200 ml methylene chloride was heated at reflux for 2 hours. The mixture was allowed to cool, solvent removed in vacuo and the residue subjected to flash chromatography to give the title compound as a low-melting white solid. PMR (CDCl3): & 1.44 (3H, t, J~6.2 Hz) 4.44 (2H, q, J~4.4 Hz), 7.44 (1H, d, J~8.1 Hz), 8.27 (1H, dd, J~8.1 Hz, 3 Hz), 9.02 (1H, d, J~3 Hz). |
Here is a chemical reaction formula: Reactants are m2:I, amount is: 0.0 ;m1:[I-].[Na+], amount is: 0.0 ;m3:ClC1=NC=C(C(=O)O)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CC(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:IC1=NC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 27.97 g (186.6 mmol) of sodium iodide cooled to -78° C. was added 121.77 g (71.6 ml, 952.0 mmol) of hydriodic acid (57 wt %). The reaction mixture was allowed to warm slightly with stirring for 5 minutes, and then 30.00 g (190.4 mmol) of 6-chloronicotinic acid was added. The resulting mixture was allowed to warm to room temperature with stirring and then heated at 120°-125° C. in an oil bath for 42 hours. A dark brown layer formed above the yellow solid material. The reaction mixture was allowed to cool to room temperature and then poured into acetone (chilled to 0° C.). The resultant yellow solid was collected by filtration, washed with 200 ml of 1N NaHSO3 solution, and dried in high vacuum (3 mm Hg) to give the title compound as a pale yellow solid. |
Here is a chemical reaction formula: Reactants are m3_m6:C(C)O, amount is: 0.0 ;m2_m5:Cl.CN(CCCN=C=NCC)C, amount is: 0.0 ;m1_m4:IC1=NC=C(C(=O)O)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:ClCCl, amount is: 0.0 ;m1_m4:ClCCl, amount is: 0.0 ,Catalysts are m3_m6:CN(C1=CC=NC=C1)C, amount is: 0.0 .Products are 0:IC1=NC=C(C(=O)OCC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 23.38 g (94.2 mmol) of 6-iodonicotinic acid in 100 ml of dichloromethane was added a solution of 19.86 g (103.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 250 ml of dichloromethane. To this suspension was added 12.40 g (15.8 ml, 269.3 mmol) of ethanol (95%) and 1.15 g (9.4 mmol) of 4-dimethylaminopyridine. The resulting solution mixture was then heated at 50° C. in an oil bath for 24.5 hours, concentrated in vacuo, partitioned between 200 ml of water and 250 ml of ethyl ether, and the layers were separated. The aqueous phase was washed with 2×150 ml-portions of ethyl ether. All organic phases were combined, washed once with 75 ml of brine solution, dried over MgSO4, filtered and concentrated in vacuo to a yellow solid. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) yielded the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4:C(#C)C1=CC=C2C(CCC(C2=C1)=O)(C)C, amount is: 0.0 ;m1_m2_m3_m4:C(#C)C1=CC=C2C(CCC(C2=C1)=O)(C)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:CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1), 4 g (21.7 mmol) of 7-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound L) was converted into the title compound using 6 g (21.7 mmol) of ethyl 4-iodobenzoate, 5 g (7.2 mmol) of bis(triphenylphosphine)palladium(II) chloride and 1.4 g (7.2 mmol) of cuprous iodide. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4:C1(CCCCC1)OC1CCC(C2=CC=C(C=C12)C#C)(C)C, amount is: 0.0 ;m1_m2_m3_m4:C1(CCCCC1)OC1CCC(C2=CC=C(C=C12)C#C)(C)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:C1(CCCCC1)OC1C=2C=C(C=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1), 90 mg (0.3 mmol) of 4-cyclohexyloxy-6-ethynyl-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound N) was converted into the title compound using 88 mg (0.32 mmol) of ethyl 4-iodobenzoate, 70 mg (0.1 mmol) of bis(triphenylphosphine)palladium(II) chloride and 19 mg (0.1 mmol) of cuprous iodide. |
Here is a chemical reaction formula: Reactants are m3:[Li+].[OH-], amount is: 0.0 ;m1_m2_m4_m5:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 ;m1_m2_m4_m5:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4_m5:C1CCOC1, amount is: 0.0 ;m1_m2_m4_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 0.30 g (0.87 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1) in 4 ml of THF and 2 ml of ethanol was added 2 ml (2 mmol) of LiOH (1N aqueous solution). The reaction mixture was stirred at room temperature for 4 hours, concentrated in vacuo to near dryness, partitioned between EtOAc and 1 ml of water and acidified to pH 4 with 10% HCl. The aqueous layer was extracted with EtOAc and then the organic layer was dried over Na2SO4 and concentrated in vacuo to give the title compound as a light yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 ;m1_m2_m3_m4:CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=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:CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl) ethynyl]benzoic acid (Compound 7), 500 mg (1.45 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoate (Compound 2) was converted into the title compound using 4 ml (4 mmol) of LiOH (1 N aqueous solution). |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m5_m3:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 ;m1_m2_m4_m5_m3:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 MOLE;m1_m2_m4_m5_m3:[BH4-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m5_m3:C1CCOC1, amount is: 0.0 ;m1_m2_m4_m5_m3:C(C)O, amount is: 0.0 ;m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a cold solution (0° C.) of 980 mg (2.8 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1) in 5 ml of THF and 10 ml of ethanol was added 78 mg (2 mmol) of sodium borohydride. The mixture was stirred for 6 hours, diluted with water (10 ml) and extracted with Et2O (4×40 ml). The combined organic layers were washed with 10% HCl (5 ml), 10% aqueous NaHCO3 (10 ml) and brine (20 ml), dried over MgSO4 and concentrated in vacuo to give the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1, amount is: 0.0 MOLE;m1_m2_m3_m4:OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 ;m1_m2_m3_m4:CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=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:OC1C=2C=C(C=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9), 1 g (2.88 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoate (Compound 2) (was converted into the title compound using 60 mg (1.6 mmol) of sodium borohydride. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1, amount is: 0.0 MOLE;m1_m2_m3_m4:OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=C(C=CC12)C#CC1=NC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 ;m1_m2_m3_m4:CC1(CCC(C=2C=C(C=CC12)C#CC1=NC=C(C(=O)OCC)C=C1)=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:OC1C=2C=C(C=CC2C(CC1)(C)C)C#CC1=NC=C(C(=O)OCC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9), 700 mg (2 mmol) of ethyl 6-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinate (Compound 4) was converted into the title compound using 60 mg (1.6 mmol) of sodium borohydride. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=C(C=CC12)C#CC1=NC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 ;m1_m2_m3_m4:CC1(CCC(C=2C=C(C=CC12)C#CC1=NC=C(C(=O)OCC)C=C1)=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:CC1(CCC(C=2C=C(C=CC12)C#CC1=NC=C(C(=O)O)C=C1)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of 4-[[5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl]ethynyl]benzoic acid (Compound 7), 300 mg (0.86 mmol) of ethyl 6-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]nicotinate (Compound 3) was converted into the title compound (pale yellow solid) using 8.6 ml (8.6 mmol) of LiOH (1M aqueous solution). |
Here is a chemical reaction formula: Reactants are m4:Cl[Si](C)(C)C, amount is: 0.0 ;m1_m2_m5_m3:OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1, amount is: 0.0 ;m1_m2_m5_m3:OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1, amount is: 0.0 MOLE;m1_m2_m5_m3:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)O[Si](C)(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 0.23 g (0.54 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9) in 4 ml of dry CH2Cl2 was added 0.06 ml of triethylamine (0.81 mmol). The solution was flushed with nitrogen and then 0.12 g (0.81 mmol) of chlorotrimethylsilane was slowly added by syringe. The mixture was stirred at room temperature (flushed with nitrogen) for 30 minutes, concentrated in vacuo to an oil and purified by flash chromatography (silica, 10% EtOAc-hexane) to yield the title compound as a clear oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)O[Si](C)(C)C)C, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)O[Si](C)(C)C)C, amount is: 0.0 MOLE;m1_m2_m3_m4:OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m2_m3_m4:OC1C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)O)C=C1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)O[Si](C)(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-trimethylsiloxynaphth-2-yl)ethynyl]benzoate (Compound 111), 83 mg (0.26 mmol) of 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoic acid (Compound 42) was converted into the title compound (white solid) using 0.07 ml (0.65 mmol) of triethylamine and 0.08 ml (0.65 mmol) of chlorotrimethylsilane. |
Here is a chemical reaction formula: Reactants are m1_m2_m6_m3_m4_m5:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C, amount is: 0.0 ;m1_m2_m6_m3_m4_m5:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)O)C=C1)=O)C, amount is: 0.0 MOLE;m1_m2_m6_m3_m4_m5:CN(C)C1=NC=CC=C1, amount is: 0.0 ;m1_m2_m6_m3_m4_m5:C[Si](C)(C)C(C)O, amount is: 0.0 ;m1_m2_m6_m3_m4_m5:Cl.CN(CCCN=C=NCC)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m6_m3_m4_m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 0.24 g (0.73 mmol) of 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid (Compound 7) in 10 ml of dry CH2Cl2 was added 0.09 g (0.74 mmol) of dimethylaminopyridine, 0.115 ml (0.80 mmol) of trimethylsilylethanol and 0.17 g (0.88 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. The reaction mixture was stirred at 25° C. for 5 hours, washed with sat. aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to an oil. Purification by flash chromatography (silica, 10% EtOAc-hexane) yielded the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC, amount is: 0.0 MOLE;m1_m2_m3_m4:OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)=O)C, amount is: 0.0 ;m1_m2_m3_m4:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)=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:OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)CC(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoate (Compound 113), 0.38 g (0.89 mmol) of trimethylsilylethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 116), was converted into the title compound (yellow solid) using 0.50 g (7.65 mmol) of zinc, 0.20 ml (1.78 mmol) of ethyl bromoacetate and 20 ml of dry benzene. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:OC1(C=2C=CC(=C(C2C(CC1)(C)C)C)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)C(=O)OCC, amount is: 0.0 ;m1_m2_m4_m3:OC1(C=2C=CC(=C(C2C(CC1)(C)C)C)C#CC1=CC=C(C(=O)OCC[Si](C)(C)C)C=C1)C(=O)OCC, amount is: 0.0 MOLE;m1_m2_m4_m3:[F-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)O)C=C1)CC(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 0.25 g (0.49 mmol) of trimethylsilylethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxy-methylnaphth-2-yl)ethynyl]benzoate (Compound 117) in 5 ml of dry THF (flushed with argon) was added 1.48 ml (1.5 mmol) of tetrabutyl ammonium fluoride (1M solution in THF). The reaction mixture was stirred at room temperature for 12 hours, concentrated in vacuo to an oil and slowly diluted with water. The solution was acidified to pH 4 with 10% HCl and extracted with Et2O. The organic layer was dried over Na2SO4, concentrated in vacuo to an oil and purified by flash chromatography (silica, 90% EtOAc-hexane) to give the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC, amount is: 0.0 MOLE;m1_m2_m3_m4:OC1(C=2C=CC(=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC, amount is: 0.0 MOLE;m1_m2_m3_m4:CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=O)C, amount is: 0.0 ;m1_m2_m3_m4:CC1(CCC(C=2C=C(C=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)=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:OC1(C=2C=C(C=CC2C(CC1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)CC(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of ethyl 4-[(7,8-dihydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoate (Compound 113), 1.00 g (2.88 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoate (Compound 2) was converted into the title compound (light yellow solid) using 1.00 g (15.30 mmol) of zinc, 0.639 ml (5.76 mmol) of ethyl bromoacetate and 70 ml of dry benzene. |
Here is a chemical reaction formula: Reactants are m1_m2_m6_m3_m4:CC1(CCCC=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)C, amount is: 0.0 ;m1_m2_m6_m3_m4:CC1(CCCC=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)C, amount is: 0.0 MOLE;m1_m2_m6_m3_m4:BrN1C(CCC1=O)=O, amount is: 0.0 ;m1_m2_m6_m3_m4:C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O, amount is: 0.0 ;m5:C(C)(=S)[O-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m6_m3_m4:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1(CCC(C=2C=CC(=CC12)C#CC1=CC=C(C(=O)OCC)C=C1)C(C)=S)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 543 mg (1.64 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (obtainable from Compound M by coupling with ethyl-4-iodobenzoate) in 20 ml of CCl4 was added 320 mg (1.81 mmol) of N-bromosuccinimide and 26 mg (0.11 mmol) of benzoyl peroxide. The mixture was refluxed for 3 hours under argon atmosphere, cooled, filtered through celite and concentrated in vacuo to a dark brown syrup. The syrup was taken up in 20 ml of dry THF and 780 mg (6.9 mmol) of potassium thioacetate was added. The mixture was refluxed for 4 hours under argon atmosphere, concentrated in vacuo and purified by chromatography (silica, 10% EtOAc-hexane) to yield the title compound as a pale yellow solid. |
Here is a chemical reaction formula: Reactants are m4_m1:CC(C)([O-])C.[Na+], amount is: 0.0 ;m2_m3:BrC(C(F)(F)F)Cl, amount is: 0.0 ;m2_m3:C(C=C(C)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m1:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC(C(C=C(C)C)O)(C(F)(F)F)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tetrahydrofuran (230 ml) and sodium t-butoxide (57.6 g; 40% w/v solution in dimethylformamide) was charged to a split-neck reaction flask, and cooled to -60° C. with stirring. 1-Bromo-1-chloro-2,2,2-trifluorethane (47.6 g) and senecialdehyde (20.9 g) were charged simultaneously over 25 minutes, then the mixture was stirred at -60° C. for a further 30 minutes. On completion of reaction, the mass was quenched by controlled addition of saturated ammonium chloride solution (120 ml). Hexane (500 ml) was added to the mixture, then the aqueous phase was separated and extracted with further hexane (2×500 ml). The combined organics were washed with brine (2×100 ml) and then water (3×20 ml). Drying (sodium sulphate) and concentration in vacuo then gave the product 5-bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene as a mobile yellow oil (50.1 g, 70% yield). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrC(C(C=C(C)C)O)(C(F)(F)F)Cl, amount is: 0.0 ;m1_m2_m3:C(C)(OC)(OC)OC, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2_m3:O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3], amount is: 0.0 .Products are 0:BrC(C=CC(CC(=O)OC)(C)C)(C(F)(F)F)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (10.0 g), trimethyl orthoacetate (16.0 g) and Montmorillonite KSF (0.5 g) were charged to a round-bottomed flask fitted with: nitrogen inlet/bubbler, thermometer and still-head. The mixture was heated with agitation, and the methanol-trimethyl orthoacetate distillates were collected until the reactor temperature increased to 111° C. (ca. 1 hr). The reaction was then heated to 135° C. and held for a further 1 hour. The methanol/trimethyl orthoacetate distillates were recharged and the distillation procedure repeated twice. Once the reaction was complete, the Montmorillonite was removed by filtration. The residual trimethyl orthoacetate was then removed by distillation under vacuum (ca. 50° C. @ 100 mmHg) to give the product, methyl 6-bromo-6-chloro-3,3-dimethyl-7,7,7-trifluorohept-4-enoate as a brown oil (7.8 g, 59% yield). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(OCC)(OCC)OCC, amount is: 0.0 ;m1_m2_m3:ClC(C(C=C(C)C)O)(C(F)(F)F)Cl, amount is: 0.0 ;m1_m2_m3:C(C(C)C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC(C=CC(CC(=O)OCC)(C)C)(C(F)(F)F)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of triethyl orthoacetate (25 ml), 5,5-dichloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (3.5 g), and isobutyric acid (0.11 g) was heated at the reflux temperature. The refluxing volatiles were condensed and collected in a Dean & Stark apparatus containing molecular sieves (4A) to collect the by-product ethanol and separate it from the orthoacetate which was returned to the mixture. After 30 minutes the more volatile components were removed by evaporation under reduced pressure and the residual oil (consisting principally of 5,5-dichloro-4-(1,1-diethoxyethoxy)-2-methyl-6,6,6-trifluorohex-2-ene, 3.8 g) collected. This was then heated with isobutyric acid (10 μl) at the reflux temperature for 16 hours under a condenser containing molecular sieves (4A) to remove ethanol from the condensate. The residual oil was subjected to purification by column chromatography using a 15:1 (by volume) mixture of hexane:ethyl acetate as eluant and a silica gel column (230-400 mesh, 60 Å) to obtain ethyl 6,6-dichloro-3,3-dimethyl-7,7,7-trifluorohept-4-enoate, identified by nuclear magnetic resonance, and gas chromatographic mass-spectroscopy. |
Here is a chemical reaction formula: Reactants are m1_m4:[H-].[Na+], amount is: 0.0 ;m2_m5:CC1(OC(C(O1)CO)CO)C, amount is: 0.0 ;m3_m7:ClCC(CC(=O)OCC)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:O1CCCC1, amount is: 0.0 ;m2_m5:O1CCCC1, amount is: 0.0 ;m3_m7:O1CCCC1, amount is: 0.0 ,Catalysts are m6:S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:C(C)OC(CC(COCC1OC(OC1COCC(CC(=O)OCC)=O)(C)C)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of sodium hydride (4.0 g, 60% dispersion in oil) in tetrahydrofuran (150 mL) under a nitrogen atmosphere was added a solution of 2,2-dimethyl-[1,3]dioxolane-4,5-dimethanol (VII, 4.05 g) in tetrahydrofuran (25 mL) over 2 min at room temperature, followed by solid tetrabutylammonium hydrogen sulfate (0.4 g). The resulting mixture was cooled in an ice bath and a solution of ethyl 4-chloroacetoacetate (VIII, 8.1 g) in tetrahydrofuran (25 mL) was added dropwise over a period of 15 min. The reaction mixture was warmed to room temperature over 1 h then refluxed for 6 h. On cooling to room temperature, the reaction mixture was quenched with 1N hydrochloric acid (20 mL) and volatile materials were removed under reduced pressure. The aqueous phase was extracted with ethyl acetate (3×30 mL). The combined organic fractions was washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (grade 9385, Merck, 230-400 mesh, 60 Å) using a mixture of hexane and ethyl acetate (8:2, 7:3 and 6:4; 500 mL each) as eluent, thereby affording the title compound (IX 4.5 g) as an oil and the mono O-alkylated compound, 4-(2-chlorophenyl)-2-(5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy-methyl-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (X, 1.95 g). Compound IX. IR (neat, cm-1): 1723, 1636; MS (CI): 436 (100%, [M+NH4 ]+). Compound X. IR (neat, cm-1): 3455, 1734; |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:COC(=O)C1=C(NC(=C(C1C1=C(C=CC=C1)Cl)C(=O)OCC)COCC=O)C, amount is: 0.0 ;m1_m2_m3_m4:Cl.O[NH3+], 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:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C=1C(C(=C(NC1C)COCC=NO)C(=O)OCC)C1=C(C=CC=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-(2-chlorophenyl)-2-methyl-6-(2-oxo-ethoxymethyl)-1,4-dihydro-3,5-pyridinedicarboxylic acid 5-ethyl 3-methyl ester (ID, 6.2 g), hydroxylammonium hydrochloride (1.27 g) and triethylamine (1.85 g) in methanol (100 mL) was stirred at room temperature for 6 h. Methanol was removed under reduced pressure and the residue was dissolved in ethyl acetate (200 mL) and water (200 mL). With vigorous stirring, the pH of the mixture was adjusted to 10 with aqueous 1N sodium hydroxide solution. After stirring for a further 15 min, the organic layer was collected, dried (sodium sulfate), filtered and concentrated in vacuo. The residue was recristallized from ether and hexane to give the title compound IB (6.1 g). HRMS: calc. for C20 H23CIN2O6 422.1245 found 422.1248; m.p. 161.4°-162.2° C.; IR (KBr, cm-1): 3446, 3379, 1698, 1671, 1601. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:COC(=O)C=1C(C(=C(NC1C)COCC=NO)C(=O)OCC)C1=C(C=CC=C1)Cl, amount is: 0.0 ;m1_m4_m2_m3:C(=O)[O-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:CO, amount is: 0.0 ,Catalysts are m1_m4_m2_m3:[OH-].[OH-].[Pd+2], amount is: 0.0 .Products are 0:COC(=O)C=1C(C(=C(NC1C)COCCN)C(=O)OCC)C1=C(C=CC=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-(2-chlorophenyl)-2-(2-hydroxyimino-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (IBa, 150 mg), palladium hydroxide on carbon (10 mg) and ammonium formate (224 mg) in methanol (10 mL) was refluxed for 5 h under a nitrogen atmosphere. On cooling to room temperature, the mixture was filtered through a pad of celite. The filtrate was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (grade 9385, Merck, 230-400 mesh, 60 Å) using a solvent mixture of dichloromethane and methanol (9:1; 100 mL), and dichloromethane, methanol and ammonium hydroxide (90:10:1; 500 mL) as eluent afforded the title compound (IAa 88 mg). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC(=O)C=1C(C(=C(NC1C)COCC(OC)OC)C(=O)OCC)C1=C(C=CC=C1)Cl, amount is: 0.0 ;m1_m3_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C=1C(C(=C2COC=CN2C1C)C(=O)OCC)C1=C(C=CC=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-(2-chlorophenyl)-2-(2,2-dimethoxy-ethoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (XX, 9.2 g) in tetrahydrofuran (200 mL) was added 3N hydrochloric acid (40 mL). The mixture was then refluxed for 4 h. On cooling to room temperature, tetrahydrofuran was removed under reduced pressure and the residue taken up in ethyl acetate (200 mL). The organic phase was washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (grade 9385, Merck, 230-400 mesh, 60 Å) using a solvent mixture of hexane and ethyl acetate as eluent (90:10; 1L) as eluent to afford the title compound (XXI 5.2 g). 1H-NMR (CDCl3) δ (ppm): 1.22 (t, 3H, J=7.1 Hz), 2.43 (s, 3H), 3.68 (s, 3H), 4.12 (q, 2H, J=7. 1 Hz),4,60(d,1H, J=13.5 Hz), 5.48 (s, 1H), 5.70 (d, 1H, J=13.8 Hz), 6.21 (d, 1H, J=4.7 Hz), 6.30(d, 1H, J=4.6 Hz), 7.07-7.28 (m, 4H); 13C-NMR (CDCl3) δ (ppm): 14.1, 15.7, 36.6, 51.2, 60.6, 63.5, 105.8, 106.7, 107.8, 127.3, 127.8, 129.5, 130.4, 131.8, 132.5 139.2, 142.0, 143.4, 166.4, 168.1; HRMS: calc. for C20H20CIN2O5 389.1030 found 389.1020; Elemental Analysis (%): calc. (found) C 61.62 (61.78), H 5.17 (5.27), N 3.59 (3.51); M.p. 126.0°-126.8° C.; IR (KBr, cm-1): 1693, 1662, 1645, 1581. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=C(C=O)C=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:ClCC(CC(=O)OCC)=O, amount is: 0.0 ;m1_m2_m3_m4:COC(C=C(C)NCCO)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C1C2(N(C(=C(C1C1=C(C=CC=C1)Cl)C(=O)OCC)CCl)CCO2)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-chlorobenzaldehyde (XI, 57.0 g), ethyl 4-chloroacetoacetate (VIII, 69.3 g) and 3-(2-hydroxyethylamino)-but-2-enoic acid methyl ester (XXIII, 63.2 g) in methanol (800 mL) was stirred at room temperature for 48 h. Methanol was removed under reduced pressure and the residue dissolved in ethyl acetate (400 mL). The organic phase was washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (grade 9385, Merck, 230-400 mesh, 60 Å) using a solvent mixture of hexane and ethyl acetate as eluent (95:5, 90:10, 85:15, 80:20, 70:30 and 60:40) as eluent afforded the title compound (XXIV 30.0 g). 1H-NMR (CDCl3) δ (ppm): 0.80 (t, 3H, J=6.9 Hz), 1.05 (s, 3H), 3.73 (s, 3H), 3.39 (s, 1H), 3.74-4.09 (m, 4H), 4.06 (q, 2H, J=6.9 Hz), 4.51 (d, 1H, J=11.5 Hz),4.63 (s, 1H), 5.40 (d, 1H, J=11.5 Hz), 7.12-7.40 (m, 4H); 13C-NMR (CDCl3) δ (ppm): 13.6, 25.7, 39.3, 39.7, 45.8, 51.0, 51.7, 59.5, 63.4, 90.5, 98.6, 126.3, 126.8, 129.6, 129.9, 133.6, 140.7, 149.5, 167.5, 171.8; HRMS: calc. for C20H23Cl2 NO2 427.0953 found 427.0939; Elemental Analysis (%): calc. (found) C 56.09 (56.12), H 5.41 (5.26), N 3.27 (3.07); m.p. 141.9°-142.8° C.; IR(KBr, cm-1): 1742, 1676, 1581, 1566. |
Here is a chemical reaction formula: Reactants are m1_m2:C1(=C(C=CC=C1)CC(C(=O)O)CC)C1=CC=CC=C1, amount is: 0.0 ;m1_m2:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C1(=C(C=CC=C1)CC(C(=O)Cl)CC)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 100-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a thermometer and a NaOH trap was charged with 13.3 g (52.4 mmol) of 3-(2-biphenylyl)-2-ethylpropionic acid and 25.9 ml (355 mmol) of thionyl chloride, and the resulting mixture was stirred under reflux for 2.5 hours under a nitrogen atmosphere. After the reaction was completed, the unreacted thionyl chloride was distilled off under reduced pressure to obtain 15.2 g of a crude product as a yellow-orange liquid. The thus obtained acid chloride was used in the next reaction without further purification. |
Here is a chemical reaction formula: Reactants are m2:C(C)C1C(C2=CC=CC(=C2C1)C1=CC=CC=C1)=O, amount is: 0.0 ;m3:[BH4-].[Na+], amount is: 0.0 MOLE;m1_m6:[BH4-].[Na+], amount is: 0.0 ;m4:CC(=O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:C(C)O, amount is: 0.0 ;m1_m6:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)C=1C(C2=CC=CC(=C2C1)C1=CC=CC=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 200-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 0.85 g (22.6 mmol) of sodium borohydride and 28 ml of ethanol. To the mixture was dropwise added a solution containing 10.6 g (45.1 mmol) of the above-obtained 2-ethyl-4-phenyl-1-indanone dissolved in 20 ml of ethanol at room temperature under a nitrogen atmosphere. After the addition was completed, the temperature of was elevated to 50° C., and the reaction mixture was stirred for 3.5 hours. After the reaction was completed, the unreacted sodium borohydride was decomposed by acetone. Then, the reaction mixture was concentrated under reduced pressure, and then dissolved in 50 ml of water and extracted with 50 ml of ether. After the organic phase was separated, the aqueous phase was extracted with 50 ml of ether two times. The combined organic phase was washed with 100 ml of a saturated aqueous solution of sodium chloride, followed by drying over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain 10.67 g of the desired product as a pasty pale yellow liquid (mixture of two kinds of isomers) (yield; 99%). |
Here is a chemical reaction formula: Reactants are m1_m2:BrC1=C(C=CC=C1)CC(C(=O)O)CCC, amount is: 277.0 MILLIMOLE;m1_m2:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:BrC1=C(C=CC=C1)CC(C(=O)Cl)CCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 500-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a thermometer and a NaOH trap was charged with 277 mmol of 3-(2-bromophenyl)-2-propylpropionic acid and 200 ml of thionyl chloride, and the mixture was heated under reflux for 2 hours. Then, the excess thionyl chloride was removed by a single distillation, and the distillation of the residue under reduced pressure gave 77.4 g of a crude product having a boiling point of 130° to 135° C./1 mmHg as a pale brown transparent liquid. This acid chloride was used in the next reaction without further purification |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m6:BrC1=C(C=O)C=CC=C1, amount is: 0.0 ;m1_m2_m3_m4_m6:C(C)C(C(C(=O)O)O)(C(=O)O)CC, amount is: 0.0 ;m1_m2_m3_m4_m6:N1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4_m6:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m6:C1=CC=CC=C1, amount is: 0.0 ;m5:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC1=C(C=CCC(C(=O)O)(C(=O)O)CC)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 500-ml three-necked round flask (Dean & Stark) equipped with a stirring bar, a Dimroth condenser and a thermometer was charged with 74.0 g (400 mmol) of 2-bromobenzaldehyde, 70.48 g (440 mmol) of diethylmaloic acid, 1.6 ml of piperidine, 4.8 ml of acetic acid and 80 ml of benzene. The mixture was subjected to azeotoropic dehydration for 7 hours in an oil bath of 110° C. under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature and 300 ml of ether was added, followed by washing with 100 ml of water two times. The organic phase was dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure and the concentrate of a orange liquid was distilled under reduced pressure to obtain 117.2 g of the desired product as a yellow liquid (yield: 90%). |
Here is a chemical reaction formula: Reactants are m2:BrC1=C2CC(C(C2=CC=C1)=O)CC(C)C, amount is: 0.0 ;m1_m4:B.[Na], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)O, amount is: 0.0 ;m1_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC1=C2CC(C(C2=CC=C1)O)CC(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 300-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 2.51 g (66.3 mmol) of sodium boron hydride and 85 ml of ethanol. To the mixture was added dropwise a solution containing 37.0 g (132.6 mmol) of the above-obtained 4-bromo-2-i-butyl-1-indanone dissolved in 55 ml of ethanol at room temperature under a nitrogen atmosphere. After the addition was completed, the mixture was further stirred for 16 hours. Then, the reaction mixture was concentrated under reduced pressure, which was then extracted with 150 ml of water and 150 ml of ether. The organic phase was separated, and the aqueous phase was further extracted with 100 ml of ether. The combined organic phase was washed with 100 ml of a saturated NaCl aq. two times, followed by dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain 34.4 g of the desired product (mixture of two isomers) as a pale yellow solid (yield: 96%). This alcohol was used in the next reaction without further purification. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m1_m2_m5_m7:C(C(C)C)C=1C(C2=CC=CC(=C2C1)C1=CC=CC2=CC=CC=C12)O, amount is: 0.0 ;m1_m2_m5_m7:C(C)N(CC)CC, amount is: 0.0 ;m3:CS(=O)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(Cl)Cl, amount is: 0.0 ;m1_m2_m5_m7:C(Cl)Cl, amount is: 0.0 ,Catalysts are m1_m2_m5_m7:CN(C1=CC=NC=C1)C, amount is: 0.0 .Products are 0:C(C(C)C)C=1CC2=CC=CC(=C2C1)C1=CC=CC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 200-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 4.54 g (14.4 mmol) of 2-i-butyl-1-hydroxy-4-(1-naphthyl)indene, 5.13 g (50.8 mmol) of triethylamine, 0.10 g (0.82 mmol) of 4-dimethylaminopyridine and 57.7 ml of methylene chloride. To the mixture was added dropwise a solution containing 3.87 ml (33.8 mmol) of methanesulfonyl chloride dissolved in 7.7 ml of methylene chloride under a nitrogen atmosphere while cooling with ice bath. After the addition was completed, the temperature was elevated to room temperature and the mixture was further stirred for 3 hours. The reaction mixture was poured onto 100 ml of water. Thereafter, the organic phase was separated, and the aqueous phase was extracted with 50 ml of methylene chloride. The extracted organic phases were combined and washed with a saturated NaCl aq., followed by dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The residue was separated and purified with silica gel chromatography (eluting with hexane/ethyl acetate (20/1 parts by volume)) to obtain 3.98 g of the desired product (mixture of two isomers) as a pale yellow pasty liquid (yield: 93%). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:OC(CNCCCCCCCC)CN(CC(CNCCCCCCCC)O)CCS(=O)(=O)O, amount is: 0.0 ;m1_m3_m2:C1(CCC(=O)O1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C=1(C(=CC=CC1)C)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC(CN(C(CCC(=O)O)=O)CCCCCCCC)CN(CC(CN(C(CCC(=O)O)=O)CCCCCCCC)O)CCS(=O)(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A reactor was charged with 27 g (0.05 mole) of 11,15-dihydroxy-13-sulfoethyl-9,13,17-triazapentacosane and 100 g of xylene, to which 12 g (0.12 mole) of succinic anhydride were then added with stirring to conduct a reaction at 50° C. for 6 hours. After xylene was distilled off under reduced pressure, 300 ml of water were added, and 10% sodium hydroxide was further added to keep the pH of the reaction mixture at 7. Thereafter, the reaction mixture was subjected to electrodialysis and lyophilized, thereby obtaining 28 g (isolation yield: 76%) of 6,10-dihydroxy-4,12-dioctyl-3,13-dioxo-8-sulfoethyl-4,8,12-triaza-1,15-pentadecanedicarboxylic acid as white crystals. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:OC(CNCCCCCCCC)CN(CC(CNCCCCCCCC)O)CCS(=O)(=O)O, amount is: 0.0 ;m1_m3_m2:C1(\C=C/C(=O)O1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C=1(C(=CC=CC1)C)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC(CN(C(C=CC(=O)O)=O)CCCCCCCC)CN(CC(CN(C(C=CC(=O)O)=O)CCCCCCCC)O)CCS(=O)(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A reactor was charged with 20 g (0.04 mole) of 11,15-dihydroxy-13-sulfoethyl-9,13,17-triazapentacosane and 100 g of xylene, to which 10 g (0.1 mole) of maleic anhydride were then added with stirring to conduct a reaction at 50° C. for 6 hours. After xylene was distilled off under reduced pressure, 300 ml of water were added, and 10% sodium hydroxide was further added to keep the pH of the reaction mixture at 7. Thereafter, the reaction mixture was subjected to electrodialysis and lyophilized, thereby obtaining 22 g (isolation yield: 80%) of 6,10-dihydroxy-4,12-dioctyl-3,13-dioxo-8-sulfoethyl-4,8,12-triaza-1,14-pentadecadiene-1,15-dicarboxylic acid as white powder. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:OC(CNCCCCCCCC)CN(CC(CNCCCCCCCC)O)CCS(=O)(=O)O, amount is: 0.0 ;m1_m3_m2:C(CO)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCCCCCC)N(C(CO)=O)CC(CN(CC(CN(C(CO)=O)CCCCCCCC)O)CCS(=O)(=O)O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A reactor was charged with 10 g (0.02 mole) of 11,15-dihydroxy-13-sulfoethyl-9,13,17-triazapentacosane, 50 ml of toluene and 5.1 ml (0.05 mole) of ethyl glycolate, and the contents were heated to 100° C. and continuously stirred for 7.5 hours while purging ethanol formed with a nitrogen stream. After completion of a reaction, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (on 200 g of silica gel, developing solvent: chloroform/methanol=100/1→20/1), thereby obtaining 10.6 g (isolation yield: 91%) of 3,11-dioctyl-2,12-dioxo-7-sulfoethyl-3,7,11-triaza-1, 5,9,13-tridecanetetraol. |
Here is a chemical reaction formula: Reactants are m4:[OH-].[Na+], amount is: 0.0 MOLE;m1_m6_m2:FC1=C(N)C=C(C(=C1)F)F, amount is: 0.0 ;m1_m6_m2:CSC, amount is: 0.0 ;m3:ClN1C(CCC1=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m6_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CSCC1=C(N)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 2,4,5-trifluoroaniline (35.0 g) are added anhydrous dichloromethane (530 ml) and dimethyl sulfide (24.6 ml) and the mixture is cooled to 0° C. Thereto N-chlorosuccinimide (38.2 g) is gradually added below 5° C. After the mixture is stirred at the same temperature for 15 minutes, triethylamine (47.7 ml) is gradually added. After reflux for 12 hours, the resultant is made alkaline with 5% aqueous sodium hydroxide solution, extracted with dichloromethane, and the extract is dried over sodium sulfate and concentrated. The residue is purified with column chlomatography (silica-gel, dichloromethane: n-hexane=1:4) to give 2-methylthiomethyl-3,4,6-trifluoroaniline (22.3 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:CSCC1=C(N)C(=CC(=C1F)F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,Catalysts are m1_m3_m2:[Ni], amount is: 0.0 .Products are 0:CC1=C(N)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 2-methylthiomethyl-3,4,6-trifluoroaniline (22.2 g) are added ethanol (400 ml) and Raney nickel (200 g) and the mixture is stirred at room temperature for 30 minutes. After the catalyst is filtered off, the filtrate is added with water and extracted with dichloromethane. The is dried over magnesium sulfate and concentrated to give 2-methyl-3,4,6-trifluoroaniline (12.3 g). |
Here is a chemical reaction formula: Reactants are m3:N(=O)[O-].[Na+], amount is: 0.0 ;m2_m8:S(O)(O)(=O)=O, amount is: 0.0 ;m6_m4_m5_m7:[C-]#N.[K+], amount is: 0.0 ;m6_m4_m5_m7:[OH-].[NH4+], amount is: 0.0 ;m1:CC1=C(N)C(=CC(=C1F)F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m8:O, amount is: 0.0 ;m6_m4_m5_m7:O, amount is: 0.0 ,Catalysts are m6_m4_m5_m7:S(=O)(=O)([O-])[O-].[Cu+2], amount is: 0.0 .Products are 0:CC1=C(C#N)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 2-methyl-3,4,6-trifluoroaniline (10.6 g) is added a mixture of conc. sulfuric acid (13.8 ml) and water (46 ml) and the mixture is cooled. Thereto an aqueous solution (20 ml) of sodium nitrite (5.5 g) is added dropwise at 0°-5° C. The solution is gradually added to a mixture of copper (II) sulfate 5 hydrate (41 g), potassium cyanide (43 g), ammonium hydroxide (60 ml) and water (260 ml) at 10°-30° C. The mixture is extracted with dichloromethane and the extract is dried over sodium sulfate, concentrated and the residue is purified with column chromatography (silica-gel, dichloromethane:n-hexane=1:4) to give 2-methyl-3,4,6-trifluorobenzonitrile (4.3 g). |
Here is a chemical reaction formula: Reactants are m1_m2:CC1=C(C(=O)O)C(=CC(=C1F)F)F, amount is: 0.0 ;m1_m2:[Cl-], amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)Cl)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 2-methyl-3,4,6-trifluorobenzoic acid (3.2 g) is added thiony chloride (7 ml) and the mixture is refluxed for 1 hour. After concentrating, 2-methyl-3,4,6-trifluorobenzoyl chloride (3.3 g) is obtained. |
Here is a chemical reaction formula: Reactants are m5_m1_m6:[Mg], amount is: 0.0 ;m4_m10:S(O)(O)(=O)=O, amount is: 0.0 ;m2_m9_m8:C(CC(=O)OCC)(=O)OCC, amount is: 0.0 ;m3_m7:CC1=C(C(=O)Cl)C(=CC(=C1F)F)F, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5_m1_m6:C(C)O, amount is: 0.0 ;m4_m10:O, amount is: 0.0 ;m2_m9_m8:C1(=CC=CC=C1)C, amount is: 0.0 ;m2_m9_m8:C(C)O, amount is: 0.0 ;m3_m7:C1(=CC=CC=C1)C, amount is: 0.0 ,Catalysts are m5_m1_m6:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 MOLE.Products are 0:CC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Separately, two drops of carbon tetrachloride are added to a solution of metallic magnesium (0.4 g) in absolute ethanol (0.9 ml). When the reaction starts, a mixture of diethyl malonate (2.6 ml), absolute ethanol (1.6 ml) and anhydrous toluene (6 ml) is added dropwise below 60° C. After stirring at 60° C. for 1 hour, the reaction mixture is cooled to 0° C. and thereto a solution of 2-methyl-3,4,6-trifluorobenzoyl chloride prepared above in toluene (5 ml) is added dropwise. After stirring for 30 minutes, a mixture of conc. sulfuric acid (0.4 ml) and water (6 ml) is added and the mixture is extracted with diethyl ether, and the extract is dried over magnesium sulfate and concentrated to give diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate (5.2 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:CC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C(=CC(=C1F)F)F, amount is: 0.0 ;m1_m3_m2:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)CC(=O)OCC)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate (5.1 g) are added water (20 ml) and p-toluenesulfonic acid (30 mg) and the mixture is refluxed for 2.5 hours. After cooling, the resultant is extracted with diethyl ether, and the extract is dried over magnesium sulfate and concentrated to give ethyl 2-methyl-3,4,6-trifluorobenzoylacetate (3.3 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:CC1=C(C(=O)CC(=O)OCC)C(=CC(=C1F)F)F, amount is: 0.0 ;m1_m2_m3:C(C)(=O)OC(C)=O, amount is: 0.0 ;m1_m2_m3:C(C)OC(OCC)OCC, 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:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To ethyl 2-methyl-3,4,6-trifluorobenzoylacetate (3.2 g) are added acetic anhydride (3.0 g) and triethoxymethane (2.7 g) and the mixture is refluxed for 1 hour. After concentrating, ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (3.5 g) is obtained. |
Here is a chemical reaction formula: Reactants are m1_m3:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F, amount is: 0.0 ;m2:C1(CC1)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (3.5 g) is dissolved in ethanol (25 ml) and thereto cyclopropylamine (0.84 ml) is added dropwise under ice-cooling. After stirring at room temperature for 30 minutes, the mixture is concentrated and the residue is purified with column chromatography (silica-gel, dichloromethane: n-hexane =1: 1) to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-cyclopropylaminoacrylate (2.7 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC, amount is: 0.0 ;m1_m3_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.9 g) are added 90% acetic acid (20 ml) and conc. hydrochloric acid (5 ml) and the mixture is refluxed for 2 hours. After cooling, the precipitated crystals are isolated, washed with water, ethanol, and diethyl ether in this order to give 1-cyclopropyl-6,7-difluoro-5-methyl-1,4,-dihydro-4-oxoquinoline-3-carboxylic acid (1.6 g), as colorless needles, m.p. 294°-298° C. |
Here is a chemical reaction formula: Reactants are m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F, amount is: 0.0 ;m2:FC1=CC=C(N)C=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:CC1=C(C(=O)C(C(=O)OCC)=CNC2=CC=C(C=C2)F)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (1.0 g) and p-fluoroaniline (0.39 g), the procedure of Reference Example 8 is repeated to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(4-fluorophenyl)aminoacrylate, which is then treated with 60% sodium hydride (0.15 g) as in Reference Example 9 to give ethyl 1-(4-fluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4- oxoquinoline-3-carboxylate (0.64 g), as white crystals (recrystallized from ethanol), m.p. 256°-259° C. |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 ;m1:FC1=CC=C(C=C1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(C=C1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 1-(4-fluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.56 g), conc. hydrochloric acid (1.5 ml), and 90% acetic acid (6 ml), the procedure of Reference Example 10 is repeated to give 1-(4-fluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.49 g), as white crystals, m.p. 255°-257° C. |
Here is a chemical reaction formula: Reactants are m2:C(C)N, amount is: 0.0 ;m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)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:CC1=C(C(=O)C(C(=O)OCC)=CNCC)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (1.0 g) and 70% aqueous ethylamine solution (0.24 ml), the procedure of Reference Example 8 is repeated to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethylaminoacrylate, which is then treated with 60 % sodium hydride (0.15 g) as in Reference Example 9 to give ethyl 1-ethyl-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.6 g), as white crystals, m.p. 157°-159° C. |
Here is a chemical reaction formula: Reactants are m1:C(C)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC, amount is: 0.0 ;m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 1-ethyl-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.55 g), conc. hydrochloric acid (1.5 ml) and 90% acetic acid (6 ml), the procedure of Reference Example 10 is repeated to give 1-ethyl-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3- carboxylic acid (0.40 g), as white crystals, m.p. >300° C. |
Here is a chemical reaction formula: Reactants are m1_m2:CC1=C(C(=O)OC)C=CC=C1[N+](=O)[O-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)(=O)O, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:CC1=C(C(=O)OC)C=CC=C1N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 2-methyl-3-nitrobenzoate (10.0 g) is dissolved in acetic acid (50 ml) and thereto 5% Pd-C (1 g) is added to carry out catalytic reduction at room temperature under 1 atm. After 1.5 hours, the catalyst is filtered off. The reaction mixture is concentrated, and thereto is added water, and the mixture is made alkaline with potassium carbonate, followed by extraction with dichloromethane. The solvent is concentrated to give methyl 2-methyl-3-aminobenzoate (8.6 g). |
Here is a chemical reaction formula: Reactants are m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F, amount is: 0.0 ;m2:FC1=C(N)C=CC(=C1)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:CC1=C(C(=O)C(C(=O)OCC)=CNC2=C(C=C(C=C2)F)F)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (1.0 g) and 2,4-difluoroaniline (0.5 g), the procedure of Reference Example 8 is repeated to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(2,4-difluorophenyl)aminoacrylate (1.1 g). |
Here is a chemical reaction formula: Reactants are m2:[H-].[Na+], amount is: 0.0 ;m1:CC1=C(C(=O)C(C(=O)OCC)=CNC2=C(C=C(C=C2)F)F)C(=CC(=C1F)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:FC1=C(C=CC(=C1)F)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(2,4-difluorophenyl)aminoacrylate (1.1 g) and 60% sodium hydride (0.13 g), the procedure of Reference Example 9 is repeated to give ethyl 1-(2,4-difluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.7 g). |
Here is a chemical reaction formula: Reactants are m1_m2:N1(CCNCC1)C=1C=C(NC2CC2)C(=C(C1F)C)[N+](=O)[O-], amount is: 0.0 ;m1_m2:C(C)OC=C(C(=O)OCC)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C1(CC1)N(C1=CC(=C(C(=C1[N+](=O)[O-])C)F)N1CCNCC1)C=C(C(=O)OCC)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 3-(1-piperazinyl)-4-fluoro-5-methyl-6-nitro-N-cyclopropylaniline (1.57 g) is added diethyl ethoxymethylenemalonate (1.45 ml) and the mixture is heated at 150° C. for 25 hours. After cooling, the reaction product is purified by silica-gel column-chromatography (dichloromethane:methanol=100:1) to give diethyl [N-cyclopropyl-N-[3-(1-piperazinyl)-4-fluoro-5-methyl-6-nitrophenyl]amino-methylene]malonate (1.50 g). The product is dissolved in acetic anhydride (7.9 ml) and thereto conc. sulfuric acid (3.16 ml) is added dropwise at 50°-60° C., followed by stirring for 30 minutes. The resultant mixture is poured into ice-water, neutralized, extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure. Purification by silica-gel column-chromatography (dichloromethane:methanol=10:1) to give ethyl 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (26 mg). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C)(C)(C)OC(=O)NC1CN(CC1C)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F, amount is: 0.0 ;m1_m3_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.NC1CN(CC1C)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture comprising 7-(3-t-butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (trans form) (120 mg), ethanol (4 ml) and 10% hydrochloric acid (4 ml) is refluxed for 30 minutes. After concentrating, the obtained residue is recrystallized from methanol-ethyl acetate to give 7-(3-amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride (trans form) (60 mg), as white powder, m.p. 272°-275° C. |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 MOLE;m1_m4_m2:N1(CCNCC1)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F, amount is: 0.0 ;m1_m4_m2:C(C)(=O)OC(C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)N1CCN(CC1)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (40 mg) in 5% sodium hydroxide (2 ml) is added acetic anhydride (0.1 ml) at room temperature. After the mixture is made acidic with dilute hydrochloric acid, the resultant is extracted with dichloromethane and the extract is dried over magnesium sulfate. After concentrating, the obtained residue is recrystallized from ethanol to give 7-(4-acetyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (29 mg), as white powder, m.p. 261°-263° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)Br)F)C)=O)C(=O)O, amount is: 0.0 ;m1_m3_m2:O=C1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CN1C(CCC1)=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)N1CCC(CC1)=O)F)C)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.58 g) in N-methyl-2-pyrrolidone (5 ml) is added 4-oxopiperidine (0.64 g) and the mixture is heated at 90° C. for 20 minutes. The solvent is distilled off under reduced pressure. To the resulting residue is added ethanol and the precipitated crystals are filtered to give 1-cyclopropyl-6-fluoro-7-(4-oxo-1-piperidinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (230 mg). |
Here is a chemical reaction formula: Reactants are m1:Cl.CN(C)CC1C(CCCC1)(O)C1=CC(=CC=C1)OC, amount is: 0.0 ;m2:[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C)CC1C(CCCC1)(O)C1=CC(=CC=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3 kg (10 mole) (1RS,2RS)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol hydrochloride (1) were suspended in 4800 ml water and treated with 1.6 kg crushed ice. 1300 ml of 36-38% (technical) caustic soda solution were added drop-wise with stirring. The mixture was subsequently extracted with 7000 ml dichloromethane, and was extracted with a further 2000 ml dichloromethane after phase separation. The combined organic phases were dried over sodium sulphate. After removing the solvent by distillation, 2630 g (99% theoretical) of (1RS,2RS)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol were obtained as a syrup. |
Here is a chemical reaction formula: Reactants are m1_m3:C(=O)(O)[C@H](O)[C@@H](O)C(=O)O.CN(C)C[C@H]1[C@](CCCC1)(O)C1=CC(=CC=C1)OC, amount is: 0.0 ;m2:[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C)C[C@H]1[C@](CCCC1)(O)C1=CC(=CC=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2050 g (4.95 mole) (1S,2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol L-(+)-tartrate from step 2 were dissolved in 4000 ml water and treated with 900 g crushed ice. 1000 ml of 36-38% (technical) caustic soda solution were added drop-wise with stirring. The mixture was subsequently extracted with 2500 ml dichloromethane, and was extracted with a further 500 ml dichloromethane after phase separation. The combined organic phases were dried over sodium sulphate. After removing the solvent by distillation, 1280 g (99% theoretical) of (1S,2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol were obtained as a syrup. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[Na+].CC(C(C(=O)[O-])=O)(C)C, amount is: 0.0 ;m1_m2_m3:Cl.NO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C(C(=O)O)=NO)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 163 g (1 mole) 93.5% trimethylpyruvic acid sodium salt and 69.5 g (1 mole) hydroxylamine hydrochloride were dissolved at 40° C. in 450 ml water. The product crystallized out during slow cooling under agitation. After 1.5 h agitation in an ice bath the crystals were filtered off, washed with 150 ml ice water, dried in a vacuum at 60° C., and then further dried in a vacuum desiccator over phosphorus pentaoxide to constant weight. 117.8 g trimethylpyruvic acid oxime (81% yield) in the form of colorless crystals were obtained. |
Here is a chemical reaction formula: Reactants are m2:O, amount is: 0.0 ;m3:C(C)OC(=O)Cl, amount is: 0.0 ;m4:[OH-].[Na+], amount is: 0.0 MOLE;m1:N[C@H](C(C)(C)C)CO, amount is: 0.25 MOLE,this reaction does not need reagents,Solvents are m5:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)[C@H]1NC(OC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 73 g (containing 0.25 mole (R)-tert-leucinol) of the filtrate cited in example 6 was taken up with 27 ml water and 200 ml toluene. 25 ml (0.26 mole) chloroformic acid ethyl ester were then added dropwise at 20°-25° C., during which the pH was maintained at 7-8.5 by the addition of 10 M sodium hydroxide solution. The mixture was then heated to 60°-65° C. at pH 8.0 and the aqueous phase separated. The toluene phase was dehydrated on a water separator under a slight vacuum and slowly heated after the addition of 0.4 g finely granulated sodium hydroxide at 70° C. A total of 40 ml distillate which contained the ethanol produced during the reaction was separated from 70°-100° C . After cooling of the batch to 65° C. a solution of 0.6 ml glacial acetic acid in 10 ml water was added, the mixture briefly agitated, the aqueous phase separated and the toluene phase compounded again with 15 ml warm water which was separated again after a brief agitation at 65° C. After distilling the organic phase on a water separator the phase was concentrated to 120 ml, filtered hot and slowly cooled off under agitation, during which the product separated in colorless crystals. These crystals were filtered off after 30 min agitation at 5° C., washed with cold toluene and dried in a vacuum at 50° C. 28.6 g (R)-4-tert-butyl-2-oxazolidinone (80% yield) was obtained. A 1H-NMR spectrum corroborated the structure of the product. |
Here is a chemical reaction formula: Reactants are m4:C1(=CC=CC=C1)C, amount is: 0.0 ;m2:OS(=O)(=O)O, amount is: 0.0 ;m1:C1=CC(=CC=C1CC2=CC=C(C=C2)F)F, amount is: 0.0 ;m3:OS(=O)(=O)O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m7_m5:O, amount is: 0.0 ;m8:O, amount is: 0.0 ,Catalysts are m7_m5:O=[Mn]=O, amount is: 0.0 .Products are 0:FC1=CC=C(C(=O)C2=CC=C(C=C2)F)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a 250 mL round bottomed flask equipped with a heating mantle, overhead agitator, thermometer, condenser, and addition funnel with a tube protruding below the liquid level was added 10.6 g 4,4'-difluorodiphenylmethane (0.051 moles). Agitation was begun and a slurry of 20.5 g MnO2 (0.195 moles) in 30 g water was added to the flask. About 30 g of water were used to wash the MnO2 beaker and were added to the flask. The mixture was allowed to reach about 100° C. at which point 50 g H2SO4 (0.487 moles) were added to the addition funnel. The H2SO4 was then added dropwise into the flask and the reaction temperature slowly rose to about 125° C. when all of the acid had been added. The mixture was heated to maintain the temperature at about 125° C. until gas chromatography showed complete conversion after approximately 12 hours. The reaction mixture was allowed to cool to 100° C. and 50 g toluene were added to the mixture. A slurry of 6 g diatomaceous earth in 30 g water was poured into a vacuum Buchner funnel fitted with No. 42 filter paper to form a filter pre-coat. The contents of the round bottomed flask were then vacuum filtered. 10 g toluene was used to wash the flask and, subsequently, the filter cake. The filter cake was then washed with 100 g toluene heated to about 50° to 70° C. and the filtrate phase separated. The toluene was removed from the organic phase by heating to approximately 65° C. at 10 mm Hg. The 10 g yellow solids assayed as 95% pure 4,4'-difluorobenzophenone for an 84% yield. The solids were recrystallized from a hexane solvent leaving 7.7 g crystalline 4,4'-difluorobenzophenone for a 68% yield. |
Here is a chemical reaction formula: Reactants are m1:C1=CC(=CC=C1CC2=CC=C(C=C2)F)F, amount is: 0.0 MOLE;m2:S(O)(O)(=O)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 MOLE,Catalysts are m3:O=[Mn]=O, amount is: 0.0 MOLE.Products are 0:FC1=CC=C(C(=O)C2=CC=C(C=C2)F)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The procedure of Example 2 is used except that the 4,4'-difluorodiphenylmethane, water, and sulfuric acid are first mixed, then heated before the MnO2 is added. The yield is 54% 4,4'-difluorobenzophenone that is 95% pure. |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 MOLE;m1_m2_m5:N1C=CC=C1, amount is: 150.0 MILLIMOLE;m1_m2_m5:COC(C(F)(F)F)O, amount is: 75.0 MILLIMOLE;m4:C1=CNC(=C1)CC2=CC=CN2, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m5:O1CCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:N1C(=CC=C1)C(C(F)(F)F)C=1NC=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Pyrrole (150 mmol) and trifluoroacetaldehyde methyl hemiacetal (75 mmol) in tetrahydrofuran are heated at reflux with catalytic amounts of hydrochloric acid for 2 hours under an inert atmosphere. GC analysis of the reaction mixture indicated the presence of the desired dipyrromethane in greater than 80% yield. Neutralization of the acid followed by work up and chromatography gave the pure bis(pyrrol-2-yl)trifluoromethylmethane 3 (R3 =CF3)). MS: m/z=214. This preparation has been disclosed in Wijesekera U.S. patent application Ser. No. 08/143,261 filed on Oct. 26, 1993. |
Here is a chemical reaction formula: Reactants are m1_m5_m2:C1C=CC2=CC=CC=C12, amount is: 0.0 ;m1_m5_m2:C(CCC)[Li], amount is: 0.0 ;m3_m4:C1(=C(C(=CC(=C1)C)C)[Si](Cl)(Cl)C1=C(C=C(C=C1C)C)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:C1CCOC1, amount is: 0.0 MOLE;m3_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=C(C(=CC(=C1)C)C)[Si](C1C=CC2=CC=CC=C12)(C1C=CC2=CC=CC=C12)C1=C(C=C(C=C1C)C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 7 g of indene in 50 cm3of THF were reacted with 24 cm3 of butyllithium (2.5-molar in hexane) at 0° C. under inert conditions. The mixture was heated to room temperature, added dropwise to a solution of 10 g of dimesityldichlorosilane in 40 cm3 of THF, and the mixture was refluxed for 4 hours. Decomposition of the batch with water, extraction with diethyl ether and chromatography on SiO2 using 2:1 toluene/hexane gave 3.28 g of dimesitylbis(indenyl)silane as a solid. MS(m/e,I rel %): 496 (100, M+); 1H NMR in CDCl3 : 2.22 ppm (12 H, s), 2.27 ppm (6 H, s), 3.40 ppm (4 H, s), 6.8-7.4 ppm (14 H, m). |
Here is a chemical reaction formula: Reactants are m2:CC(C=NC1CNCC1)(C)C, amount is: 0.0 MOLE;m3:Cl, amount is: 0.0 MOLE;m1:C1(CC1)N1C=C(C(C2=CC(=C(C(=C12)F)F)F)=O)C(=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:Cl.NC1CN(CC1)C1=C(C=C2C(C(=CN(C2=C1F)C1CC1)C(=O)O)=O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: If, for example, 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid is reacted with 3-(2,2-dimethylpropylideneamino)-pyrrolidine and the reaction product is treated with hydrochloric acid, 7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride is obtained. |
Here is a chemical reaction formula: Reactants are m2:N[C@@H]1CNCC1, amount is: 0.0 MOLE;m4:ClC=1C(=C(C=C2C(C(=CN(C12)C1CC1)C(=O)O)=O)F)N1C[C@H](CC1)N=CC1=CC(=CC=C1)[N+](=O)[O-], amount is: 0.0 MOLE;m3:ClC=1C(=C(C=C2C(C(=CN(C12)C1CC1)C(=O)O)=O)F)F, amount is: 0.0 MOLE;m1:[N+](=O)([O-])C=1C=C(C=O)C=CC1, 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:Cl.N[C@@H]1CN(CC1)C1=C(C=C2C(C(=CN(C2=C1Cl)C1CC1)C(=O)O)=O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: If, for example, the reaction mixture of 3-nitrobenzaldehyde and (S)-3-aminopyrrolidine is reacted with 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in a one-pot reaction, the course of the reaction via the intermediately formed 8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-7-[(S)-3-(3-nitrobenzylideneamino)-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid to give 7-[(S)-3-amino-1-pyrrolidinyl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride can be represented by the following equation: ##STR19## |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:NC1CNCC1, amount is: 0.0 ;m1_m4_m2_m3:C(C(C)(C)C)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C1(=CC=CC=C1)C, amount is: 0.0 ;m1_m4_m2_m3:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C=NC1CNCC1)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 34.5 g (0.4 mol) of 3-aminopyrrolidine are initially introduced into 100 ml of toluene, and 34.5 g (0.3 mol) of 75% strength pivalaldehyde (preparation from Riedel-de-Haen) in 100 ml of toluene are added dropwise at 20° C., while cooling in a water bath. The mixture is subsequently stirred at room temperature for 2 hours, the aqueous phase is then separated off in a separating funnel (4.6 ml) and the toluene solution is dried over sodium sulphate for 1 hour. The toluene is separated off on a rotary evaporator and the residue is distilled using a small Vigreux column. 46.2 g of 3-(2,2-dimethylpropylideneamino)-pyrrolidine of boiling point 61° C./10 mbar are obtained with a purity, determined by gas chromatography, of 98%, corresponding to a yield of 74% and a selectivity of 99% (pivalaldehyde). |
Here is a chemical reaction formula: Reactants are m1:C(C1=CC=CC=C1)N1CC(CC1)NCC1=CC=CC=C1, amount is: 0.0 ;m3_m4_m2:C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m4_m2:CO, amount is: 0.0 ,Catalysts are m3_m4_m2:[Pd], amount is: 0.0 MOLE.Products are 0:CC(C=NC1CNCC1)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 36.8 g (0.138 mol) of 1-benzyl-3-benzylaminopyrrolidine are hydrogenated in 160 ml of methanol over 5 g of 5% strength palladium on active charcoal at 130° C. under a hydrogen pressure of 100 bar for 10 hours. The catalyst is filtered off and 16.6 g (0.138 mol ) of 71% strength pivalaldehyde are added to the filtrate, while stirring, after which the temperature rises from 20° C. to 28° C. The mixture is subsequently stirred for 30 minutes, the methanol is removed on a rotary evaporator and the residue is distilled. 12.7 g of 3-(2,2-dimethyl-propylidene-amino)-pyrrolidine of boiling point: 61° C./10 mbar are obtained with a purity, determined by gas chromatography, of 97%, corresponding to a yield of 58% of theory. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:N[C@H](C(=O)O)CCCCO, amount is: 0.0 ;m1_m3_m2:Cl, amount is: 0.0 MOLE;m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:Cl.N[C@H](C(=O)OC)CCCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A slurry of (S)-2-amino-6-hydroxyhexanoic acid (2.42 g., 16.4 mmole) in dry methanol (60 ml.) was treated with gaseous hydrogen chloride until the mixture began to reflux. The homogeneous solution was then stirred at room temperature for 2.5 hours. The solvent was stripped and the residue azeotroped three times with toluene to give crude (S)-2-amino-6-hydroxyhexanoic acid, methyl ester, hydrochloride salt as an oil. This oil was dissolved in dimethylformamide (20 ml.) and methylene chloride (50 ml.) and treated with 4-methyl morpholine (3.20 ml., 2.94 g., 29.1 mmole). This mixture was cooled to 0° C. and treated with (S)-2-phthalimido-4-pentenoic acid [obtained from 7.0 g., 16.4 mmole of the salt product from part (a) by partitioning between 10% potassium bisulfate and ethyl acetate] in methylene chloride (10 ml.), followed by solid hydroxybenzotriazole (2.22 g., 16.4 mmole) and ethyl-3-(3-dimethylamino)propyl carbodiimide, hydrochloride salt (3.458 g., 18.0 mmole). After stirring at 0° C. for 0.5 hour and at room temperature for 2 hours, the reaction was partitioned between ethyl acetate and 0.5N hydrochloric acid. The ethyl acetate extract was washed successively with water, 50% saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped. The residue was flash chromatographed (Merck silica gel, ethyl acetate) to give pure title compound as an oil which solidified upon standing. The solid was triturated with ethyl ether and hexane and collected by filtration to give 5.149 g. of analytically pure title product; m.p. 90°-92° C.; [α]D =+25.6 (c=1.1, chloroform). TLC (ethyl acetate) Rf =0.36. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:[Br-].[K+], amount is: 0.0 ;m1_m2_m4:N[C@H](CCCC)C(=O)O, amount is: 0.0 ;m3:N(=O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:S(O)(O)(=O)=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Br[C@H](C(=O)O)CCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Potassium bromide (15.9 g., 133 mmol.) was added to a stirred solution of D-norleucine (5.0 g., 38 mmol.) in 2.5N sulfuric acid (77 ml.) at room temperature. The reaction mixture was cooled to -10° C. and solid sodium nitrite (3.94 g., 57 mmol.) was added portionwise, maintaining the temperature between -10° and -5° C. After addition was complete, the foamy reaction was stirred for 1 hour and then warmed to room temperature and stirred for another hour. The reaction mixture was then extracted twice with ether, the ether extracts were washed once with water, dried (magnesium sulfate), filtered and evaporated to give 3.3 g. of crude title product. |
Here is a chemical reaction formula: Reactants are m3:N(=O)[O-].[Na+], amount is: 0.0 ;m1_m2_m4:[Br-].[K+], amount is: 0.0 ;m1_m2_m4:N[C@H](CC(C)C)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:S(O)(O)(=O)=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Br[C@H](C(=O)O)CC(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Potassium bromide (9.5 g., 80 mmol.) was added to a stirred solution of D-leucine (3.0 g., 23 mmol.) in 2.5N sulfuric acid (47 ml.) at room temperature. The reaction mixture was cooled to -10° C. and solid sodium nitrite (2.4 g., 34 mmol.) was added portionwise, maintaining the temperature between -10° and -5° C. After addition was complete, the reaction was stirred for 1 hour and then warmed to room temperature and stirred for another hour. The reaction mixture was then extracted twice with ether, the ether extracts were washed once with water, dried (magnesium sulfate), filtered and evaporated to give 2.7 g. of crude title product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:CC(C(=O)O)=CC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 ;m1_m2_m3:CO, amount is: 0.0 ,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 MOLE.Products are 0:CC(C(=O)O)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of α-methyl cinnamic acid (10.0 g., 61.7 mmol.) in dry methanol (250 ml.) was treated with 10% palladium on carbon and hydrogenated (balloon used) at room temperature for 16 hours. The reaction mixture was diluted with methanol (250 ml.), filtered through a Celite pad in a millipore unit, washing the pad well with methanol (2×100 ml.). The clear filtrate was evaporated to dryness to give 10.225 g. of title product as a thick syrup. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:C([O-])([O-])=O.[Cs+].[Cs+], amount is: 0.0 ;m1_m2_m4_m3:C1(C=2C(C(N1[C@H](C(=O)O)CCCCO)=O)=CC=CC2)=O, amount is: 0.0 ;m1_m2_m4_m3:C(C1=CC=CC=C1)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(C=2C(C(N1[C@H](C(=O)OCC1=CC=CC=C1)CCCCO)=O)=CC=CC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A slurry of cesium carbonate (3.819 g, 11.7 mmol.) and (S)-2-phthalimido-6-hydroxyhexanoic acid (6.00 g, 21.6 mmol.) in dimethylformamide (60 ml.) was treated with benzyl bromide (3.30 ml., 4.75 g., 27.7 mmol.). After stirring at room temperature for 2 hours, the mixture was partitioned between ethyl acetate and water. The organic extract was washed with water (twice) and brine, then dried (sodium sulfate), filtered and stripped to give an oil. The oil was flash chromatographed (Merck silica gel, 6/4-ethyl acetate/hexane) to give essentially pure product as a solid. Recrystallization from ethyl acetate/hexane gave 7.173 g. (1st crop) and 394 mg. (2nd crop) for a total of 7.567 g. of pure title product; m.p. 106°-108.5° C.; [α]D =-27.5° (c=1.5, methanol). TLC (75/25 ethyl acetate/hexanes) Rf =0.43. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:C1(C=2C(C(N1[C@H](C(=O)O)CCCCO)=O)=CC=CC2)=O, amount is: 0.0 ;m1_m2_m4_m3:C([O-])([O-])=O.[Cs+].[Cs+], amount is: 0.0 ;m1_m2_m4_m3:CI, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m2_m4_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(C=2C(C(N1[C@H](C(=O)OC)CCCCO)=O)=CC=CC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A slurry of (S)-2-phthalimido-6-hydroxyhexanoic acid (3.752 g., 13.5 mmol.) and cesium carbonate (2.178 g., 6.7 mmol.) in dimethylformamide (44 ml.) was treated with methyl iodide (3.0 ml., 6.84 g., 48.2 mmol.). After stirring at room temperature for 2 hours, the mixture was diluted with ethyl acetate and washed successively with water containing a small amount of sodium bisulfite, water, 50% saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped to give the title product as a colorless oil (3.825 g.). The oil was homogeneous by |
Here is a chemical reaction formula: Reactants are m3:BrCC(=O)OCC, amount is: 0.0 ;m1_m4_m2_m5:CC(C)(OC(=O)N[C@@H]1C(N[C@@H](CCC1)C)=O)C, amount is: 0.0 ;m1_m4_m2_m5:C[Si](C)(C)[N-][Si](C)(C)C.[Li+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2_m5:O1CCCC1, amount is: 0.0 ;m1_m4_m2_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(OC(=O)N[C@@H]1C(N([C@@H](CCC1)C)CC(=O)OCC)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (3S-cis)-hexahydro-3-[[(1,1-dimethylethoxy)carbonyl]amino]-7-methyl-2H-azepin-2-one [prepared as described in Example 64(f), 500 mg., 2.06 mmol.] in tetrahydrofuran (13 ml.) at room temperature under argon was treated dropwise with 1.0M lithium bis(trimethylsilyl)amide in tetrahydrofuran (2.7 ml., 2.7 mmol.) immediately followed by the dropwise addition of ethyl bromoacetate (0.47 ml., 4.21 mmol.). The resulting mixture was stirred for 30 minutes, quenched with aqueous ammonium chloride, diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate), filtered and concentrated to a yellow oil. Following flash chromatography (E Merck silica gel) eluting with 2:1 hexane/ethyl acetate, 750 mg. of title product was obtained as a light yellow oil; TLC (1:1 ethyl acetate:hexane) Rf =0.52. |
Here is a chemical reaction formula: Reactants are m5_m8:BrCCCCCl, amount is: 0.0 ;m0_m2_m3_m6:C(C)(C)NC(C)C, amount is: 0.0 ;m0_m2_m3_m6:C(CCC)[Li], amount is: 0.0 ;m4_m7:C1(CCCC1)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m8:O1CCCC1, amount is: 0.0 MOLE;m0_m2_m3_m6:O1CCCC1, amount is: 0.0 ;m4_m7:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)[N-]C(C)C.[Li+];0:ClCCCCC1(CCCC1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of lithium diisopropylamide was prepared under nitrogen from diisopropylamine (31.0 ml., 220 mmol.) and n-butyl lithium (1.5M in hexane, 88.0 ml., 220 mmol.) in tetrahydrofuran (80 ml.), maintaining the temperature between -3° C.-1° C. After stirring 15 minutes, cyclopentanecarboxylic acid (11.4 g., 100 mmol.) in tetrahydrofuran (10 ml.) was added at 0° C.-3° C. over 25 minutes. After an additional 15 minutes at 0° C., the bath was removed and the reaction stirred 15 minutes more, causing the temperature to rise to 11° C. The milky white solution was cooled to -74° C. and 1-bromo-4-chlorobutane (23 ml., 200 mmol.) in tetrahydrofuran was added quickly, the temperature rising to -66° C. After 16 hours, the reaction was allowed to warm to room temperature in situ. The reaction was quenched with methanol (10 ml.) and concentrated in vacuo. The residue was partitioned between water (200 ml.) and ethyl ether (200 ml.). The aqueous layer was acidified to pH 1 with 12M hydrochloric acid and extracted with methylene chloride (3×150 ml.), dried (magnesium sulfate), filtered and evaporated to give 20.0 g. of the title product as a yellow oil. |
Here is a chemical reaction formula: Reactants are m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m6:O.NN, amount is: 0.0 ;m1_m2_m6:C1(C=2C(C(N1[C@H]1CCCC(NC1=O)(C)C)=O)=CC=CC2)=O, amount is: 0.0 ;m4:C1(=CC=CC=C1)C(Cl)(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m5:C1(=CC=CC=C1)C(Cl)(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m6:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@H]1CCCC(NC1=O)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Hydrazine monohydrate (4.59 ml., 94.6 mmol.) was added to a solution of (S)-hexahydro-6-phthalimido-2,2-dimethyl-2H-azepine-7-one [prepared as described in Example 66(e), 19.98 g., 68.76 mmol.] in methanol (250 ml.) at room temperature under argon. The resulting mixture was stirred for 72 hours then filtered to remove the white precipitate. The volatiles were evaporated and the residue was dissolved in methylene chloride (560 ml.) and filtered to remove additional precipitate. To this filtrate was added triethylamine (13.3 ml., 96.21 mmol.) followed by triphenylchloromethane (20.65 g., 74.07 mmol.) and the resulting mixture was stirred for 1.5 hours. Additional triphenylchloromethane (958 mg., 3.44 mmol.) was added and the solvent was removed. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried, filtered and concentrated to give a pale yellow foam. Following a crystallization from ethyl acetate and hexanes, 7.47 g. of title product was obtained as off-white crystals. The mother liquor was concentrated and crystallized from ethyl acetate and pentane to give a second crop (8.02 g.) of title product. The mother liquor was concentrated and the residue was flash chromatographed (E Merck silica gel) eluting with 4.5:5.5 ethyl acetate/hexanes to give 6.0 g of title compound as a white foam. The combined yield of title product was 21.49 g.; m.p. 139°-140° C.; [α]D =+43.4° (c=0.37, methylene chloride). TLC (2:3 hexane: ethyl acetate) Rf =0.63. |
Here is a chemical reaction formula: Reactants are m4:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE;m3:[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1, amount is: 0.0 ;m1_m2_m5:N1CCCC(C2=C1C=CC=C2)=O, amount is: 0.0 MOLE;m1_m2_m5:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 3.32 g portion of 2,3,4,5-tetrahydro-1H-1-benzazepin-5-one and 4.31 ml of triethylamine were dissolved in 33 ml of dichloromethane and, with stirring on an ice bath, 4.59 g of p-nitrobenzoyl chloride was added to the resulting solution. The reaction solution was stirred at room temperature for additional 60 minutes. The reaction solution was then mixed with a saturated sodium bicarbonate aqueous solution and subjected to phase separation. The dichloromethane layer was separated and washed with a 1N hydrochloric acid aqueous solution and a saturated sodium chloride aqueous solution once for each. The thus washed layer was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The thus obtained residue was recrystallized from methyl alcohol to obtain 5.68 g of 1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one. |
Here is a chemical reaction formula: Reactants are m1:[N+](=O)([O-])C1=CC=C(C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=C1, amount is: 0.0 MOLE;m2:CN(C=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 ,Catalysts are m3:[Ni], amount is: 0.0 .Products are 0:NC1=CC=C(C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 19.2 g portion of 1-(4-nitrobenzoyl)-2,3,4,5-tetrahydro1H-1-benzazepin-5-one was dissolved in a mixed solvent consisting of 200 ml of dimethylformamide and 100 ml of methyl alcohol, and 3 ml of Raney nickel was added to the resulting solution to carry out hydrogenation at normal pressure. After completion of the hydrogen absorption, the reaction solution was filtered and concentrated. The thus obtained residue was dissolved in dichloromethane and then washed with a saturated sodium bicarbonate aqueous solution. The resulting dichloromethane layer was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The thus obtained residue was recrystallized from methyl alcohol to obtain 15.5 g of 1-(4-aminobenzoyl)-2,3,4,5-tetrahydro1H-1-benzazepin-5-one. |
Here is a chemical reaction formula: Reactants are m1:CC1=CC=C(C=C1)C1=C(C(=O)O)C=CC=C1, amount is: 0.0 MOLE;m2:NC1=CC=C(C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=C1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1=CC=C(C=C1)C1=C(C(=O)NC2=CC=CC=C2)C=CC(=C1)C(=O)N1CCCC(C2=C1C=CC=C2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using o-(4-methylphenyl)benzoic acid and 1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one as starting materials, the procedure of Reference Example 3 was repeated to obtain 2-(4-methylphenyl)-4-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide. |
Here is a chemical reaction formula: Reactants are m2:Cl.N1=C(C=CC=C1)CC(=S)N, amount is: 0.0 ;m1:C1(=CC=CC=C1)C1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=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:N1=C(C=CC=C1)CC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 400 mg of 2-phenyl-4'-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide and 370 mg of 2-pyridylthioacetamide hydrochloride, the procedure of Example 5 was repeated, and the resulting free base was recrystallized from chloroform-diethyl ether to obtain 300 mg of 4'-[[2-(2-pyridylmethyl)-5,6-dihydro-4H-thiazolo[5,4-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide. |
Here is a chemical reaction formula: Reactants are m1:C1(=CC=CC=C1)C1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=CC=C1, amount is: 0.0 ;m2:Cl.N1=CC(=CC=C1)CC(=S)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:Cl.N1=CC(=CC=C1)CC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 400 mg of 2-phenyl-4'-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide and 400 mg of 3-pyridylthioacetamide hydrochloride, the procedure of Example 5 was repeated to obtain 100 mg of 4'-[[2-(3-pyridylmethyl)-5,6-dihydro-4H-thiazolo[5,4-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide hydrochloride as an amorphous solid. |
Here is a chemical reaction formula: Reactants are m1:C1(=CC=CC=C1)C1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=CC=C1, amount is: 0.0 ;m2:Cl.CN(C)CCNC(=S)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CN(CCNC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using 400 mg of 2-phenyl-4'-[(5-oxo-2,3,4,5-tetrahydro1H-1-benzazepin-1-yl)carbonyl]benzanilide and 300 mg of dimethylaminoethylthiourea hydrochloride and using ethyl alcohol as the reaction solvent, the procedure of Example 5 was repeated and the resulting residue was recrystallized from ethyl acetate-diethyl ether to obtain 300 mg of 4'-[(2-dimethylaminoethylamino-5,6-dihydro-4H-thiazolo[5,4-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide.2 HCl. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m6_m4:C(C)(C)(C)OC(=O)NCC(=O)O, amount is: 0.0 ;m1_m2_m3_m6_m4:ON1N=NC2=C1C=CC=C2, amount is: 0.0 ;m1_m2_m3_m6_m4:CN1CCOCC1, amount is: 0.0 ;m1_m2_m3_m6_m4:Cl.C(C)N=C=NCCCN(C)C, amount is: 0.0 ;m7_m5:Br.NC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3, amount is: 0.0 ,this reaction does not need reagents,Solvents are m8:O, amount is: 0.0 MOLE;m1_m2_m3_m6_m4:ClCCl, amount is: 0.0 ;m7_m5:ClCCl, amount is: 0.0 ;m9:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.CC(C)O.NCC(=O)NC=1SC=2CCN(C3=C(C2N1)C=CC=C3)C(=O)C3=CC=C(NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O)C=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: After dissolving 176 mg of t-butoxycarbonylglycine, 205 mg of 1-hydroxybenztriazole and 0.15 ml of N-methylmorpholine in 3.5 ml of dichloromethane, 192 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to the resulting solution with stirring on an ice bath, and the mixture was warmed up to room temperature and stirred for 60 minutes. To this reaction solution, again cooled on an ice bath, was added dropwise 4 ml of dichloromethane in which 400 mg of the 4'-[(2-amino-5,6-dihydro-4H-thiazolo[5,4-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide hydrobromide described in Example 1 and 0.103 ml of triethylamine had been dissolved, followed by overnight stirring at room temperature. The reaction solution was mixed with water, stirred for 60 minutes and then subjected to phase separation. The dichloromethane layer was separated, washed with a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution once for each and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation, the thus obtained residue was suspended in 3 ml of methyl alcohol. With cooling on an ice bath, the suspension was mixed with 4.4 ml of 4N hydrochloric acid-dioxane and stirred for 3 hours. Thereafter, the reaction solution was concentrated and the thus obtained residue was recrystallized from 2-propyl alcohol to obtain 250 mg of 4'-[(2-glycylamino-5,6-dihydro-4H-thiazolo[5,4-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide 2-propylalcohol hydrochloride. |
Here is a chemical reaction formula: Reactants are m2:Cl.C(C)(=O)OCC, amount is: 0.0 ;m1_m3:CC=1NC2=C(CCN(C3=C2C=CC=C3)C(=O)C3=CC=C(NC(C2=C(C=CC=C2)C2=CC=CC=C2)=O)C=C3)N1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.CC=1NC2=C(CCN(C3=C2C=CC=C3)C(=O)C3=CC=C(NC(C2=C(C=CC=C2)C2=CC=CC=C2)=O)C=C3)N1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4'-[(2-Methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide was dissolved in 5 ml of ethyl alcohol, the resulting solution was mixed with 0.19 ml of 4N hydrochloric acid-ethyl acetate and cooled on an ice bath and then the thus precipitated crystals were collected by filtration and washed with a small volume of ethyl alcohol to obtain 220 mg of 4'-[(2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepin-6-yl)carbonyl]-2-phenylbenzanilide hydrochloride (Example 18(2)). |
Here is a chemical reaction formula: Reactants are m2:Cl.C(C)(=O)OCC, amount is: 0.0 ;m1_m3:CC1=CC=C(C=C1)C1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCC3=C(C4=C2C=CC=C4)NC(=N3)C)C=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.CC1=CC=C(C=C1)C1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCC3=C(C4=C2C=CC=C4)NC(=N3)C)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Methylphenyl)-4'-[(2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepin-6-yl)carbonyl]benzanilide was dissolved in 10 ml of ethyl alcohol, the resulting solution was mixed with 0.37 ml of 4N hydrochloric acid-ethyl acetate and cooled on an ice bath and then the thus precipitated crystals were collected by filtration and washed with a small volume of ethyl alcohol to obtain 500 mg of 2-(4-methylphenyl)-4'-[(2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepin-6-yl)carbonyl]benzanilide hydrochloride (Example 19(2)). |
Here is a chemical reaction formula: Reactants are m2:NC1=CC=C(C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=C1, amount is: 0.0 MOLE;m1:CC1=C(C(=O)O)C=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using o-methylbenzoic acid and 1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one as starting materials, the procedure of Reference Example 3 was repeated to obtain 2-methyl-4'-[(5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide. |
Here is a chemical reaction formula: Reactants are m4_m8_m6:O=C1CCCNC2=C1C=CC=C2, amount is: 0.0 ;m2_m3:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m2_m3:CN(C=O)C, amount is: 0.0 MOLE;m1_m5:COC=1C(=CC=C(C1)C(=O)O)C1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4_m8_m6:ClCCl, amount is: 0.0 ;m4_m8_m6:C(C)N(CC)CC, amount is: 0.0 ;m1_m5:ClCCl, amount is: 0.0 ;m7:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC1=C(C2=CC=C(C=C2)C(=O)N2CCCC(C3=C2C=CC=C3)=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 1.67 g portion of 2-methoxybiphen-4-ylcarboxylic acid was dissolved in 17 ml of dichloromethane, 0.95 ml of oxalyl chloride and a catalytically effective amount of dimethylformamide were added to the resulting solution with cooling on an ice bath and then the resulting mixture was warmed up to room temperature. When completion of foaming was confirmed, the reaction solution was concentrated under a reduced pressure and subjected to azeotropic treatment with toluene twice. The thus obtained residue was dissolved in 8.4 ml of dichloromethane and, with cooling on an ice bath, the resulting solution was dropwise added to a solution obtained by dissolving 1.0 g of 5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine and 1.53 ml of triethylamine in 10 ml of dichloromethane. The reaction solution was warmed up to room temperature and the stirring was continued for 1 hour. The resulting reaction solution was mixed with water and subjected to phase separation to separate dichloromethane layer which was subsequently washed with 0.5N hydrochloric acid and a saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate. After removing the solvent by distillation, the thus obtained residue was crystallized from toluene to obtain 1.65 g of 1-(2'-methoxybiphen-4-ylcarbonyl)-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine as crude crystals. |
Here is a chemical reaction formula: Reactants are m1_m2:[Br-].[Br-].[Br-].C1(=CC=CC=C1)[N+](C)(C)C.C1(=CC=CC=C1)[N+](C)(C)C.C1(=CC=CC=C1)[N+](C)(C)C, amount is: 0.0 MOLE;m1_m2:O1CCCC1, amount is: 0.0 ;m3:O=C1CCCN(C2=C1C=CC=C2)C(=O)C2=CC=C(NC(C1=C(C=CC=C1)C(C)C)=O)C=C2, amount is: 0.0 ;m4: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:C(C)(C)OC1=C(C(=O)NC2=CC=C(C=C2)C(=O)N2CCC3=C(C4=C2C=CC=C4)NC(=N3)C)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: With cooling on an ice bath, a 793 mg portion of phenyltrimethylammonium tribromide was added to 20 ml of tetrahydrofuran solution containing 1.0 g of 4'-[(5-oxo-2,3,4,5-tetrahydro1H-1-benzazepin-1-yl)carbonyl]-2-isopropylbenzanilide, and the mixture was warmed up to room temperature. Filtration was carried out when disappearance of the color of bromine was confirmed after about 60 minutes. The filtered material was washed with tetrahydrofuran, and the filtrates were combined and concentrated. The thus obtained residue was dissolved in chloroform, washed with a sodium bicarbonate aqueous solution and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was further evaporated to dryness using a vacuum pump. The thus obtained solid substance was dissolved in 40 ml of chloroform, and the resulting solution was mixed with 1.11 g of acetamidine hydrochloride and 2.26 g of potassium carbonate and subjected to 20 hours of heating under reflux in a stream of argon. The resulting reaction solution was mixed with water to effect phase separation, and the organic layer was separated and dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was crystallized from toluene to obtain 640 mg of 2-isopropoxy-4'-[(2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepin-6-yl)carbonyl]benzanilide. A 563 mg portion of this compound was dissolved in 5.5 ml of ethyl alcohol, mixed with 0.45 ml of 4N hydrochloric acid-ethyl acetate and recrystallized to obtain 400 mg of 2-isopropyl-4'-[(2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepin-6-yl)carbonyl]benzanilide hydrochloride. |
Here is a chemical reaction formula: Reactants are m1_m3:COC1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)N1CCC2=C(C3=C1C=CC=C3)NC(=N2)C, amount is: 0.0 MOLE;m2:Cl.C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.COC1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)N1CCC2=C(C3=C1C=CC=C3)NC(=N2)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6-[(2'-Methoxy-4-biphenylyl)carbonyl]-2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine was dissolved in 4.8 ml of ethyl alcohol, the solution was mixed with 0.44 ml of 4N hydrochloric acid-ethyl acetate and cooled on an ice bath to effect crystal formation, and then the thus formed crystals were collected by filtration and washed with a small volume of ethyl alcohol to obtain 260 mg of 6-[(2'-methoxy-4-biphenylyl)carbonyl]-2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine hydrochloride (Example 33(2)). |
Here is a chemical reaction formula: Reactants are m1:C(C1=CC=CC=C1)C#N, amount is: 0.0 ;m2:BrCCCCBr, amount is: 0.0 ;m3_m4:O, amount is: 0.0 MOLE;m3_m4:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5_m6:[H-].[Na+], amount is: 0.0 MOLE;m5_m6:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C1(CCCC1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a stream of argon, 60% sodium hydride was dissolved in 10 ml of tetrahydrofuran, and the solution was mixed with 2.0 g of benzyl cyanide, stirred for 1 hour at room temperature, further mixed with 3.69 g of 1,4-dibromobutane and again stirred for 16 hours at room temperature. The reaction mixture was mixed with water and ethyl acetate, and the resulting organic layer was separated, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was subjected to silica gel column chromatography, and the resulting hexane eluate was mixed with 45 ml of sulfuric acid and subjected to 24 hours of heating under reflux. After cooling down to room temperature, the reaction solution was mixed with ice water and ethyl acetate to separate water layer which was subsequently mixed with concentrated hydrochloric acid and ethyl acetate, and the resulting organic layer was separated, washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. By removing the solvent by distillation under a reduced pressure, 978 mg of 1-phenylcyclopentanecarboxylic acid was obtained. |