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Here is a chemical reaction formula: Reactants are m1_m2:C(C)OC(=O)CCCOC1=CC=C(C=C1)S(=O)(=O)N=C=O, amount is: 0.0 ;m1_m2:NC1=C(C(=O)O)C=CC(=C1)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:ClC1=CC=C2C(N(C(NC2=C1)=O)S(=O)(=O)C1=CC=C(C=C1)OCCCC(=O)OCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 763 mg (2.44 mmol) of 4-(3-ethyloxycarbonylpropyloxy)benzenesulfonylisocyanate and 418 mg (2.44 mmol) of 2-amino-4-chlorobenzoic acid were treated in the same way as in Example 1 to obtain 306 mg of the above-identified compound (yield 27.0%). Properties: colorless crystal, Melting point: 167°-169° C., PMR (δppm, DMSO-d6):1.18 (3H,s), 1.98-2.03 (1H,m), 2.46 (2H,t), 4.04-4.14 (4H,m), 7.12 (1H,s), 7.16 (2H,d), 7.21 (1H,d), 7.85 (1H,d), 8.09 (2H,d), 11.58 (1H,s). |
Here is a chemical reaction formula: Reactants are m2:C(#N)C1=C(C=CC=C1)S(=O)(=O)N, amount is: 0.0 MOLE;m1:ClC1=CC(=C(C(=O)OCC)C=C1)NC(=O)OC1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(#N)C1=C(C=CC=C1)S(=O)(=O)NC(=O)NC1=C(C=CC(=C1)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: As the starting substances, ethyl 4-chloro-2-phenoxycarbonylaminobenzoate and 2-cyanobenzenesulfonamide were used and the same method was applied as in Example 36 to obtain N-(2-cyanobenzenesulfonyl)-N'-(2-ethyloxycarbonyl-5-chlorophenyl)urea and further to obtain from 1.52 g (3.73 mmol) of N-(2-cyanobenzenesulfonyl)-N'-(2-carboxyl-5-chlorophenyl)urea 810 mg of the above-identified compound (yield 60.1%). Properties: colorless crystal, Melting point: 160°-161° C., PMR (δppm, DMSO-d6):3.71 (3H,s), 6.61 (1H,s), 6.90 (1H,s), 7.12 (1H,s), 7.23 (1H,d), 7.72 (1H,s), 7.86 (1H,d), 11.59 (1H,br). |
Here is a chemical reaction formula: Reactants are m1:ClC1=CC(=C(C(=O)OCC)C=C1)NC(=O)OC1=CC=CC=C1, amount is: 0.0 MOLE;m2:O1CCN(CC1)CCOC1=CC=C(C=C1)S(=O)(=O)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:O1CCN(CC1)CCOC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1=C(C=CC(=C1)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: As the starting substances, ethyl 4-chloro-2-phenoxycarbonylaminobenzoate and 4-(2-morpholinoethyloxy)benzenesulfonamide were used and the same method was applied as in Example 36 to obtain N-[4-(2-morpholinoethyloxy)benzenesulfonyl]-N'-(2-ethyloxycarbonyl-5-chlorophenyl)urea and further to obtain from 500 mg (0.98 mmol) of N-[4-(2-morpholinoethyloxy)benzenesulfonyl)-N'-(2-carboxyl-5-chlorophenyl)urea 120 mg of the above-identified compound (yield 27.2%). Properties: colorless crystal, Melting point: >200° C. (decomposition), PMR (δppm, DMSO-d6):2.48 (4H,t), 2.73 (2H,t), 3.57 (4H,t), 4.22 (2H,t), 7.12 (1H,s), 7.20 (3H,t), 7.85 (1H,d), 8.09 (2H,d), 11.56 (1H,br). |
Here is a chemical reaction formula: Reactants are m1:ClC1=CC(=C(C(=O)OCC)C=C1)NC(=O)OC1=CC=CC=C1, amount is: 0.0 MOLE;m2:BrCCOC1=CC=C(C=C1)S(=O)(=O)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:BrCCOC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1=C(C=CC(=C1)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: As the starting substances, ethyl 4-chloro-2-phenoxycarbonylaminobenzoate and 4-(2-bromoethyloxy) benzenesulfonamide were used and the same method was applied as in Example 36 to obtain N-[4-(2-bromoethyloxy)benzenesulfonyl]-N'-(2-ethyloxycarbonyl-5-chlorophenyl)urea and further to obtain from 760 mg (1.50 mmol) of N-[4-(2-bromoethyloxy)benzenesulfonyl]-N'-(2-carboxyl-5-chlorophenyl)urea 320 mg of the above-identified compound (yield 46.4%). Properties: colorless crystal, Melting point: >200° C. (decomposition), PMR (δppm, DMSO-d6):3.82 (2H,t), 4.46 (2H,t), 7.12 (1H,s), 7.12-7.23 (3H,m), 7.85 (1H,d), 8.11 (2H,d), 11.59 (1H,s). |
Here is a chemical reaction formula: Reactants are m1:ClC1=CC(=C(C(=O)OCC)C=C1)NC(=O)OC1=CC=CC=C1, amount is: 0.0 MOLE;m2:C1(=CC=CC=C1)N1CCN(CC1)CCOC1=CC=C(C=C1)S(=O)(=O)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)N1CCN(CC1)CCOC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1=C(C=CC(=C1)Cl)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: As the starting substances, ethyl 4-chloro-2-phenoxycarbonylaminobenzoate and 4-[2-(4-phenylpiperazin-1-yl)ethyloxy)benzenesulfonamide were used and the same method was applied as in Example 36 to obtain N-{4-[2-(4-phenylpiperazin-1-yl)ethyloxy] benzenesulfonyl}-N'-(2-ethyloxycarbonyl-5-chlorophenyl)urea and to obtain from 813 mg (1.39 mmol) of N-{4-(2-(4-phenylpiperazin-1-yl)ethyloxy] benzenesulfonyl}-N'-(2-carboxy-5-chlorophenyl)urea 115 mg of the above-identified compound (yield 15.3%). Properties: colorless crystal, Melting point: 177°-179° C., PMR (δppm, DMSO-d6):2.65 (4H,t), 2.80 (2H,t), 3.13 (4H,t), 4.26 (2H,t), 6.75 (1H,t), 6.90 (2H,d), 7.12 (1H,s), 7.17-7.22 (5H,m), 7.85 (1H,d), 8.10 (2H,d), 11.59 (1H,br). |
Here is a chemical reaction formula: Reactants are m1:ClC1=CC(=C(C(=O)OCC)C=C1)NC(=O)OC1=CC=CC=C1, amount is: 0.0 MOLE;m2:ClC1=CC(=C(C=C1)S(=O)(=O)N)C#N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=CC(=C(C=C1)S(=O)(=O)NC(=O)NC1=C(C=CC(=C1)Cl)C(=O)OCC)C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: As the starting substances, ethyl 4-chloro-2-phenoxycarbonylaminobenzoate and 4-chloro-2-cyanobenzenesulfonamide were used and the same method was applied as in Example 36 to obtain N-(4-chloro-2-cyanobenzenesulfonyl)-N'-(2-ethyloxycarbonyl-5-chlorophenyl)urea and further to obtain from 1.04 g (2.35 mmol) of N-(4-chloro-2-cyanobenzenesulfonyl)-N'-(2-carboxy-5-chlorophenyl)urea 31 mg of the above-identified compound (yield 3.3%). Properties: colorless crystal, Melting point: >200° C. (decomposition), PMR (δppm, DMSO-d6):7.32-7.36 (2H,m), 7.99 (1H,d), 8.05 (1H,d), 8.38 (1H,d), 8.54 (1H,s), 12.16 (1H,br). |
Here is a chemical reaction formula: Reactants are m1:ClC1=CC(=C(C(=O)OC)C=C1)NC(=O)OC1=CC=CC=C1, amount is: 0.0 MOLE;m2:NC1=CC=C(C=C1)S(=O)(=O)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:NC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1=C(C=CC(=C1)Cl)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: As the starting substances, methyl 4-chloro-2-phenoxycarbonylaminobenzoate and 4-aminobenzenesulfonamide were used and the same method was applied as in Example 36 to obtain N-(4-aminobenzenesulfonyl)-N'-(2-methoxycarbonyl-5-chlorophenyl)urea and further to obtain from 470 mg (1.27 mmol) of N-(4-aminobenzenesulfonyl)-N'-(2-carboxy-5-chlorophenyl)urea 270 mg of the above-identified compound (yield 60.5%). Properties: colorless crystal, Melting point: >250° C. (decomposition), PMR (δppm, DMSO-d6):6.39 (2H,s), 6.63 (2H,d), 7.09 (1H,s), 7.22 (2H,d), 7.76 (2H,d), 7.83 (2H,d), 11.51 (1H,s). |
Here is a chemical reaction formula: Reactants are m1:ClC1=CC(=C(C(=O)OC)C=C1)NC(=O)OC1=CC=CC=C1, amount is: 0.0 MOLE;m2:C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1=C(C=CC(=C1)Cl)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: As the starting substances, methyl 4-chloro-2-phenoxycarbonylaminobenzoate and 4-acetylbenzenesulfonamide were used and the same method was applied as in Example 36 to obtain N-(4-acetylbenzenesulfonyl)-N'-(2-methoxycarbonyl-5-chlorophenyl)urea and further to obtain from 300 mg (0.76 mmol) of N-(4-acetylbenzenesulfonyl)-N'-(2-carboxyl-5-chlorophenyl)urea 170 mg of the above-identified compound (yield 59.1%). Properties: colorless crystal, Melting point: >250° C. (decomposition), PMR (δppm, DMSO-d6):2.64 (3H,s), 7.10 (1H,s), 7.24 (1H,q), 7.85 (1H,d), 8.17 (2H,d), 8.27 (2H,d). |
Here is a chemical reaction formula: Reactants are m1:ClC1=CC(=C(C(=O)OC)C=C1)NC(=O)OC1=CC=CC=C1, amount is: 0.0 MOLE;m2:N1N=NN=C1C1=CC=C(C=C1)S(=O)(=O)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:N1N=NN=C1C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1=C(C=CC(=C1)Cl)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: As the starting substances, methyl 4-chloro-2-phenoxycarbonylaminobenzoate and 4-(5-tetrazolyl) benzenesulfonamide were used and the same method was applied as in Example 36 to obtain N-[4-(5-tetrazolyl)benzenesulfonyl]-N'-(2-methoxycarbonyl-5-chlorophenyl)urea and further to obtain from 2.00 g (4.44 mmol) of N-[4-(5-tetrazolyl)benzenesulfonyl]-N'-(2-carboxyl-5-chlorophenyl)urea 602 mg of the above-identified compound (yield 33.5%). Properties: colorless crystal, Melting point: >200° C. (decomposition), PMR (δppm, DMSO-d6):7.14 (1H,s), 7.24 (1H,d), 7.87 (2H,d), 8.34 (4H,q), 11.66 (1H,br). |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=NC2=CC=CC=C2C=C1, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:N1=C(C=CC2=CC=CC=C12)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-aminophenylthio)quinoline(3.9 mmoles, 1.0 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (3.9 mmoles, 0.92 g) were reacted according to procedure A to yield 1.06 g, 56% of the title compound. Mass spec (FD) 490. Calculated for C23H15ClF3 N3S2 : C, 56.38; H, 3.09, N, 8.58. Found: C, 56.60; H, 3.11; N, 8.42. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=NC2=CC=CC=C2C=C1, amount is: 0.0 ;m1_m2_m3_m4:NC1=CC=C(C=C1)S, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=CC=C(C=C1)SC1=NC2=CC=CC=C2C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chloroquinoline (0.04 moles, 6.54 g), 4-aminothiophenol (0.04 moles, 5.0 g) and potassium carbonate (0.04 moles, 5.52 g) were stirred at room temperature in 200 ml of ethanol for 18 hr. The reaction mixture was concentrated, ethyl acetate was added and the solution washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with ethyl acetate/hexane to yield 2-(4-aminophenylthio)quinoline 4.0 g, 40%. Mass Spec (FD) 252. Calculated for C15H12N2S: C, 71.40; H, 4.79, N, 11.10. Found: C, 71.11; H, 4.98N, 11.20. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=NC2=CC=CC=C2C(=C1)C(=O)OCC, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)OC(=O)C1=CC(=NC2=CC=CC=C12)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-aminophenylthio)-4-ethoxycarbonylquinoline (6.0 mmoles, 2.0 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (6.0 mmoles, 1.4 g) were reacted according to procedure C to yield 3.0 g, 89% of the title compound. Mass Spec (FD) 561. Calculated for C26H19ClF3 N3O2S2 : C, 55.56; H, 3.41; N, 7.48. Found: C, 55.38H, 3.38; N, 7.36. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=NC2=CC=C(C=C2C=C1)Cl, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:ClC=1C=C2C=CC(=NC2=CC1)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Aminophenylthio)-6-chloroquinoline (2.9 mmoles, 0.83 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (3.2 mmoles, 0.76 g) were reacted according to procedure C to yield 0.78 g, 51% of the title compound. Mass Spec (FD) 524. Calculated for C23H14ClF3 N3S2 : C, 52.68; H, 2.69; N, 8.01. Found: C, 52.66; H, 2.78; N, 7.91. M Pt 138°-1390° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=NC2=CC=C(C=C2C=C1)Cl, amount is: 0.0 ;m1_m2_m3:NC1=CC=C(C=C1)S, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2_m3:CN(C)C=1C=CN=CC1, amount is: 0.0 .Products are 0:NC1=CC=C(C=C1)SC1=NC2=CC=C(C=C2C=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2,6-Dichloroquinoline (15.2 mmoles, 3.0 g), 4-aminothiophenol (15.2 mmoles, 1.9 g), and DMAP 15.2 mmoles, 1.85 g) were stirred at room temperature for 3 days. The solvent was removed, diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 25% ethyl acetate in hexane to yield 2-(4-aminophenylthio)-6-chloroquinoline 830 mg, 19%. Mass spec (FD) 286. Calculated. for C15H11ClN2S: C, 62.82H, 3.87; N, 9.77. Found: C, 63.09; H, 3.94; N, 9.61. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:C1(=CC=CC=C1)C1=CC(=NC2=CC=CC=C12)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-aminophenylthio)-4-phenylquinoline (3.0 mmoles, 1.0 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (3.3 mmoles, 0.79 g) were reacted according to procedure C to yield the title compound 1.03 g, 61%. Mass Spec (FD) 565. Calculated for C29H19ClF3N3 S2 : C, 61.53; H, 3.38; N, 7.42. Found: C, 61.82; H, 3.63; N, 7.43. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m5:ClC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m4_m5:NC1=CC=C(C=C1)S, amount is: 0.0 ;m3:C1CCOC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m5:C(C)O, amount is: 0.0 ,Catalysts are m1_m2_m4_m5:CN(C)C=1C=CN=CC1, amount is: 0.0 .Products are 0:NC1=CC=C(C=C1)SC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chloro-4-phenylquinoline (4.18 mmoles, 10.0 g), 4-aminothiophenol (41.8 mmoles, 5.2 g) and DMAP (41.8 mmoles, 5.0 g) were stirred in 200 ml ethanol and 50 ml THF for 3 days. The solution was concentrated, ethyl acetate added, washed with water, dried over sodium sulfate and the solvent removed. The product was purified by HPLC over silica gel eluted with 30% ethyl acetate in hexane to yield 2-(4-aminophenylthio)-4-phenylquinoline 6.2 g, 45%. Mass Spec (FD) 328. Calculated for C21H16N2S: C, 76.80; H, 4.91N, 8.53. Found: C, 77.04; H, 5.00; N, 8.55. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=NC2=CC=C(C=C2C=C1)OC, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:COC=1C=C2C=CC(=NC2=CC1)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-aminophenylthio)-6-methoxyquinoline 15.0 mmoles, 4.2 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate 15.0 mmoles, 3.6 g) were reacted according to procedure C to yield 5.6 g, 72% of the title compound. Mass Spec (FD) 519. Calculated for C24H17ClF3 N3OS2 : C, 55.44; H, 3.30; N, 8.08. Found: C, 55.62; H, 3.43; N, 8.27. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=NC2=CC=C(C=C2C=C1)OC, amount is: 0.0 ;m1_m2_m3_m4:NC1=CC=C(C=C1)S, amount is: 0.0 ;m1_m2_m3_m4:CN(C)C1=NC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=CC=C(C=C1)SC1=NC2=CC=C(C=C2C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chloro-6-methoxyquinoline (52.0 mmoles, 10.0 g), 4-aminothiophenol (52.0 mmoles, 6.5 g) and dimethylaminopyridine (52.0 mmoles, 6.3 g) were stirred for 16 hr in 250 ml ethanol. The reaction was condensed and purified by HPLC over silica gel eluted with 25-30% ethyl acetate/hexane to yield 2-(4-aminophenylthio)-6-methoxyquinoline. 8.5 g, 58% product. Mass spec (FD) 282. Calculated for C16H14N2OS: C, 68.06; H, 5.00, N, 9.92. Found: C, 68.04; H, 4.97; N, 10.02. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=CC=NC2=CC=CC=C12, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:N1=CC=C(C2=CC=CC=C12)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(4-aminophenylthio)quinoline (3.9 mmoles, 1.0 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (3.9 mmoles, 0.92 g) were reacted according to procedure A to yield of the title compound 1.06 g, 56%. Mass spec (FD) 490. Calculated for C23H15ClF3 N3S2 : C, 56.38; H, 3.09, N, 8.58. Found: C, 56.60; H, 3.11; N, 8.42. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=CC=NC2=CC=CC=C12, amount is: 0.0 ;m1_m2_m3_m4:[N+](=O)([O-])C1=CC=C(C=C1)S, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C=C1)SC1=CC=NC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Chloroquinoline (32.3 mmoles, 5.2 g), 4-nitrothiophenol (32.3 mmoles, 5.0 g) and potassium carbonate (32.3 mmoles, 4.46 g) were stirred at room temperature in 500 ml of ethanol for 16 hr. The reaction mixture was then concentrated, ethyl acetate was added and the solution washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 20-40% ethyl acetate/hexane to yield 4-(4-nitrophenylthio)quinoline 4.9 g, 54%. Mass Spec (FD) 282. Calculated for C15H10N2O2S: C, 63.82H, 3.57N, 9.92. Found: C, 65.09; H, 3.81; N, 10.02. |
Here is a chemical reaction formula: Reactants are m1_m2:[N+](=O)([O-])C1=CC=C(C=C1)SC1=CC=NC2=CC=CC=C12, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)O, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:NC1=CC=C(C=C1)SC1=CC=NC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(4-nitrophenylthio)quinoline 17.0 mmoles, 4.9 g) was dissolved in 200 ml ethanol and hydrogenated over 5 g of 5% Pd/C at 40 psi for 1 hr at room temperature. The solution was filtered through celite and the solvent removed to yield 4-(4-aminophenylthio)quinoline 2.5 g, 58%. Mass spec (FD) 253. Calculated for C15H12N2S: C, 71.40; H, 4.79, N, 11.10. Found: C, 71.12; H, 4.93N, 10.88. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=CC=NC2=CC(=CC=C12)C(F)(F)F, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:FC(C1=CC=C2C(=CC=NC2=C1)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(4-aminophenylthio)-7-trifluoromethylquinoline (0.01 mole, 3.2 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (0.01 mole, 2.4 g) were reacted according to procedure C to yield the title compound 3.5 g, 63%. Mass Spec (FD) 557. Calculated for C24H14ClF6N3 S2 : C, 51.66; H, 2.53; N, 7.53. Found: C, 51.92; H, 2.53; N, 7.46. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=CC=NC2=CC(=CC=C12)C(F)(F)F, amount is: 0.0 ;m1_m2_m3_m4:NC1=CC=C(C=C1)S, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,Catalysts are m1_m2_m3_m4:CN(C1=CC=NC=C1)C, amount is: 0.0 .Products are 0:NC1=CC=C(C=C1)SC1=CC=NC2=CC(=CC=C12)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Chloro-7-trifluoromethylquinoline (0.043 moles, 10.0 g), 4-aminothiophenol (0.043 moles, 5.3 g) and 4-dimethylaminopyridine (0.04 moles, 4.9 g) were stirred in 250 ml ethanol for 3 days. The reaction mixture was filtered, concentrated, ethyl acetate added, washed with water and dried over sodium sulfate. The solution was concentrated and the product purified by HPLC over silica gel eluted with 25% ethyl acetate/hexane to yield 4-(4-aminophenylthio)-7-trifluoromethylquinoline 10.2 g, 74%. Mass Spec (FD) 320. Calculated for C16H11F3 N2S: C, 59.99; H, 3.46; N. 8.74. Found: C, 60.08; H, 3.49; N, 8.77. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=CC2=CC=CC=C2C=C1, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:C1=C(C=CC2=CC=CC=C12)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Aminophenylthio)naphthalene (4.2 mmoles, 1.06 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (4.2 mmoles, 0.93 g) were reacted according to procedure A to yield of the title compound 0.7 g, 34%. Mass Spec (FD) 489. Calculated for C24H16ClF3 N2S2 : C, ; H, N, . Found: C, ; H, ; N, . |
Here is a chemical reaction formula: Reactants are m1_m3:[N+](=O)([O-])C1=CC=C(C=C1)SC1=CC2=CC=CC=C2C=C1, amount is: 0.0 ;m2_m4: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 ,Catalysts are m2_m4:[Pd], amount is: 0.0 .Products are 0:NC1=CC=C(C=C1)SC1=CC2=CC=CC=C2C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-nitrophenylthio)naphthalene (9.2 mmoles, 2.6 g) was dissolved in 50 ml ethanol and 20 ml ethyl acetate and hydrogenated for 16 hrs at room temperature over 1.0 g 5% Pd/C. The solution was filtered through celite and concentrated to yield 2-(4-aminophenylthio)naphthalene 1.1 g, 47%. |
Here is a chemical reaction formula: Reactants are m1_m2:[N+](=O)([O-])C1=CC=C(C=C1)SC1=CC=CC2=CC=CC=C12, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)(=O)OCC, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:NC1=CC=C(C=C1)SC1=CC=CC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-(4-Nitrophenylthio)naphthalene (39.0 mmoles, 11.0 g) was dissolved in 200 ml ethyl acetate and hydrogenated over 8 g of 5% Pd/C at 40 psi for 1 hr at room temperature. The solution was filtered through celite and the solvent removed to yield 1-(4-aminophenylthio)naphthalene 9.0 g, 92%. Mass spec (FD) 251. Calculated for C15H17NS: C, 76.46; H, 5.21, N, 5.57 Found: C, 76.71; H, 5.39; N, 5.47. |
Here is a chemical reaction formula: Reactants are m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(F)F, amount is: 0.0 ;m1:[N+](=O)([O-])C1=CC=C(C=C1)SC=1NC2=C(N1)C=CC=C2, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)OCC, amount is: 0.0 MOLE,Catalysts are m4:[Pd], amount is: 0.0 .Products are 0:N1=C(NC2=C1C=CC=C2)SC2=CC=C(C=C2)NC(=S)NC2=CC(=C(C=C2)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Nitrophenylthio)benzimidazole (5.0 mmoles, 1.37 g) was reduced in ethyl acetate over 1.37 g 5% Pd/C, filtered and condensed and then reacted with 4-chloro-3-trifluoromethylphenylisothiocyanate (5.0 mmoles, 1.0 g) according to procedure C to yield the title compound 0.12 g, 5% product. Mass Spec (FD) 479. Calculated for C21H14ClF3N4 S2 : C, 52.66; H, 2.95; N, 11.70. Found: C, 52.85; H, 3.18; N, 10.47. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC=1NC2=C(N1)C=CC=C2, amount is: 0.0 ;m1_m2_m3_m4:[N+](=O)([O-])C1=CC=C(C=C1)S, amount is: 0.0 ;m1_m2_m3_m4:C1CCC2=NCCCN2CC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C=C1)SC=1NC2=C(N1)C=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chlorobenzimidazole (0.033 moles, 5.0 g), 4-nitrothiophenol (0.033 moles, 4.14 g), and DBU (0.033 moles, 5.0 g) in 200 ml ethanol were heated at 55° C. for 3 hr. The reaction was concentrated, ethyl acetate added, washed with water, dried over sodium sulfate and the solvent removed. The solid was slurred in hexane to yield 2-(4-nitrophenylthio)benzimidazole 1.37 g, 15%. Mass Spec (FD) 271. Calculated for C13H8N3O2S: C, 57.55; H, 3.34; N, 15.49. Found: C, 57.50; H, 5.54; N, 15.23. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC=1OC2=C(N1)C=CC=C2, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:O1C(=NC2=C1C=CC=C2)SC2=CC=C(C=C2)NC(=S)NC2=CC(=C(C=C2)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Aminophenylthio)benzoxazole (10.0 mmoles, 2.6 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (10.0 mmoles, 2.4 g) were reacted according to procedure A to yield of the title compound 1.6 g, 33%. Mass Spec (FD) 479. Calculated for C21H13ClF3 N3OS2 : C, 52.56; H, 2.73; N, 8.75. Found: C, 52.47; H, 2.70; N, 8.48. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC=1OC2=C(N1)C=CC=C2, amount is: 0.0 ;m1_m2_m3_m4:NC1=CC=C(C=C1)S, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=CC=C(C=C1)SC=1OC2=C(N1)C=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chlorobenzoxazole (0.065 moles, 10.0 g), 4-aminothiophenol (0.065 moles, 8.1 g) and potassium carbonate (0.065 moles, 9.0 g) were stirred for 3 days at room temperature in 250 ml ethanol, filtered, and concentrated. Ethyl acetate was added and the solution washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 50% ethyl acetate in hexane to yield 2-(4-aminophenylthio)benzoxazole 12.5 g, 79%. Mass spec (FD) 243. Calculated for C11H10N2OS: C, 64.44; H, 4.16; N, 11.56. Found: C, 64.53; H, 4.22; N, 11.58. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC=1SC2=C(N1)C=CC=C2, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:S1C(=NC2=C1C=CC=C2)SC2=CC=C(C=C2)NC(=S)NC2=CC(=C(C=C2)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Aminophenylthio)benzothiazole (10.0 mmoles, 2.6 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate 10.0 mmoles, 2.4 g) were reacted according to procedure C to yield of the title compound, 1.5 g, 30%. Mass Spec (FD) 495. Calculated for C21H13ClF3 N3S3 : C, 50.85H, 2.64N, 8.47. Found: C, 51.02; H, 2.71; N, 8.31. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC=1SC2=C(N1)C=CC=C2, amount is: 0.0 ;m1_m2_m3_m4:NC1=CC=C(C=C1)S, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=CC=C(C=C1)SC=1SC2=C(N1)C=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chlorobenzothiazole (0.06 moles, 10.1 g), 4-aminothiophenol (0.06 moles, 7.5 g) and potassium carbonate (0.06 moles, 8.3 g) were stirred for 3 days at room temperature in 250 ml ethanol, filtered, and concentrated. Ethyl acetate was added and the solution washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 40-60% ethyl acetate in hexane to yield 2-(4-aminophenylthio)benzothiazole 13.7 g, 88%. Mass spec (FD) 258. Calculated for C11H10N2S2 : C, 60.44; H, 3.90; N, 10.84. Found: C, 60.63; H, 3.98; N, 11.01. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC=1SC2=C(N1)C=C(C=C2)Cl, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:ClC=1C=CC2=C(N=C(S2)SC2=CC=C(C=C2)NC(=S)NC2=CC(=C(C=C2)Cl)C(F)(F)F)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-aminophenylthio)-5-chlorobenzothiazole (5.5 mmoles, 1.6 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (5.5 mmoles, 1.3 g) were reacted according to procedure C to yield the title compound 0.7 g, 24%. Mass Spec (FD) 529. Calculated for C21H12Cl2F3 S3 : C, 47.55; H, 2.28; N, 7.92. Found: C, 47.55; H, 3.32; N, 7.87. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC=1SC2=C(N1)C=C(C=C2)Cl, amount is: 0.0 ;m1_m2_m3_m4:NC1=CC=C(C=C1)S, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,Catalysts are m1_m2_m3_m4:CN(C)C=1C=CN=CC1, amount is: 0.0 .Products are 0:NC1=CC=C(C=C1)SC=1SC2=C(N1)C=C(C=C2)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2,5-Dichlorobenzothiazole (0.049 moles, 10.0 g), 4-aminothiophenol (0.049 moles, 6.1 g) and DMAP (0.049 moles, 6.0 g) were stirred for 3 days at room temperature in 250 ml ethanol, filtered, and concentrated. Ethyl acetate was added and the solution washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 25% ethyl acetate in hexane to yield 2-(4-aminophenylthio)-5-chlorobenzothiazole 3.2 g, 22%. Mass spec (FD) 292. Calculated for C13H9ClN2S2 : C, 53.33; H, 3.10; N, 9.57. Found: C, 53.03; H, 3.30; N, 9.70. |
Here is a chemical reaction formula: Reactants are m2_m4:CN(C)C=O, amount is: 0.0 ;m1_m3:[N+](=O)([O-])C1=CC=C(C=C1)C=1C(=NC2=CC=CC=C2C1)S(=O)(=O)C1=NC2=CC=CC=C2C=C1C1=CC=C(C=C1)[N+](=O)[O-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ,Catalysts are m2_m4:[Pd], amount is: 0.0 .Products are 0:NC1=CC=C(C=C1)S(=O)C1=NC2=CC=CC=C2C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Nitrophenyl-2-quinolylsulfone (9.0 mmoles, 2.7 g) was dissolved in 200 ml ethanol and 75 ml DMF and was then hydrogenated over 2.2 g 5% Pd/C at room temperature for 3 hr. The reaction mixture was then filtered through celite and condensed to afford 2-(4-aminophenylsulfinyl)quinoline |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)NC1=NC2=CC=CC=C2C=C1, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:N1=C(C=CC2=CC=CC=C12)NC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-aminophenylamino)quinoline (5.0 mmoles, 1.15 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (5.0 mmoles, 1.20 g) were reacted according to procedure C of to yield the title compound 1.60 g, 68%. Mass Spec (FD) 473. Calculated for C23H16ClF3 N4S: C, ; H, ; N, . Found: C, ; H, ; N, . |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(OC2=NC3=CC=CC=C3C=C2)C=C1, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:N1=C(C=CC2=CC=CC=C12)OC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Aminophenoxy)quinoline (2.4 mmoles, 0.56 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (2.4 mmoles, 0.57 g) were reacted according to procedure C to yield the title compound, 0.8 g. 70%. Mass Spec (FD) 473. Calculated for C23H15ClF3N3OS: C, 58.29; H, 3.19; N, 8.87. Found: C, 58.47; H, 3.48; N, 8.85. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m3:ClC1=NC2=CC=CC=C2C=C1, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 MOLE;m1_m5:[N+](=O)([O-])C1=CC=C(C=C1)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(OC2=NC3=CC=CC=C3C=C2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Nitrophenol(41 mmoles, 5.1 g) was dissolved in DMF (500 ml) and treated with sodium hydride (41 mmoles previously washed with hexane). After stirring at room temperature for 1 hr, 2-chloroquinoline (40 mmoles, 6.5 g) was added dropwise and stirred for 16 hr at room temperature followed by refluxing for 6 hr. Water was added to the cooled solution and the product was extracted with ethyl acetate. The ethyl acetate solution was washed with water, and 5N NaOH, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with ethyl acetate/hexane to yield 2-(4-nitrophenoxy)quinoline. 3.1 mmoles, 8%. Mass Spec (FD) 266. Calcd for C15H10N2O3 : C 67.45; H, 3.84; N, 10.40. Found: C, 65.84; H, 3.88; N, 8.47. |
Here is a chemical reaction formula: Reactants are m1_m2:[N+](=O)([O-])C1=CC=C(OC2=NC3=CC=CC=C3C=C2)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)(=O)OCC, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:NC1=CC=C(OC2=NC3=CC=CC=C3C=C2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Nitrophenoxy)quinoline(3 mmoles, 0.82 g) was dissolved in 100 ml ethyl acetate and hydrogenated over 2.0 g 5% Pd/C at room temperature for 1 hr. The solution was filtered through cellulose and concentrated to yield 2-(4-aminophenoxy)quinoline 0.58, 82%. Mass Spec (FD) 236. Calculated for C15H12N2O: C, 76.25; H, 5.12, N, 11.86. Found: C, 75.97; H, 5.37; N, 11.83. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=NC2=CC=CC=C2C=C1, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=O)C(F)(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:N1=C(C=CC2=CC=CC=C12)SC1=CC=C(C=C1)NC(=O)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Aminophenylthio)quinoline (3.9 mmoles, 1.0 g) and 4-chloro-3-trifluoromethylphenylisocyanate (3.9 mmoles, 0.85 g) were reacted according to procedure A to yield the title compound, 0.8 g, 43%. Mass Spec (FD) 463. Calculated for C23H15ClF3N3OS: C, 58.29; H, 3.19; N, 8.87. Found: C, 58.56; H, 3.43; N. 9.02. M Pt 194°-195° C. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=NC2=CC=CC=C2C=C1, amount is: 0.0 ;m1_m2:ClC=1C=C(C=CC1Cl)N=C=S, 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=CC2=CC=CC=C12)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Aminophenylthio)quinoline 11.9 mmoles, 3.0 g) and 3,4-dichlorophenylisothiocyanate 11.9 mmoles, 2.42 g) were reacted according to procedure B to yield the title compound, 360 mg, 6.6%. Mass Spec (FD) 455. Calculated for C22H15Cl2N3S2 : C, 57.90 H. 3.31; N, 9.21. Found: C, 57.86; H, 3.53; N, 9.07. m.p. 125°-126°. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC1=NC2=CC=CC=C2C=C1, amount is: 0.0 ;m1_m2_m3_m4:[N+](=O)([O-])C1=CC=C(C=C1)S, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C=C1)SC1=NC2=CC=CC=C2C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chloroquinoline (0.12 moles, 20.0 g), 4-nitrothiophenol (0.13 mmoles, 20.8 g), and potassium carbonate (0.13 moles, 18.5 g) were dissolved in 800 ml ethanol and stirred at room temperature for 1.5 hr. The mixture was filtered and the solid washed with ethanol. The solid was dissolved with ethyl acetate, washed with water, dried over sodium sulfate and concentrated to yield 2-(4-nitrophenylthio)quinoline 26.0 g, 77%. Mass Spec (FD) 282. Calculated for C15H10N2O2S: C, 63.82, H 3.57; N, 9.92. Found: C, 63.55, H 3.59; N, 9.71. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[N+](=O)([O-])C1=CC=C(C=C1)SC1=NC2=CC=CC=C2C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CN(C)C=O, amount is: 0.0 ,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 .Products are 0:NC1=CC=C(C=C1)SC1=NC2=CC=CC=C2C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Nitrophenylthio)quinoline (0.42 moles, 12.0 g) was hydrogenated in 300 ml DMF over 5.0 g Pd/C for 3 hr at room temperature. The solution was filtered through celite and concentrated. The product was triturated with ether and hexane to yield 2-(4-aminophenylthio)quinoline 10.0 g, 93%. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC=1N=NC(=CC1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:C1(=CC=CC=C1)C1=CC=C(N=N1)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-(4-aminophenylthio)-6-phenylpyridazine (7.0 mmoles, 2.0 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (7.0 mmoles, 1.66 g) were reacted according to procedure C to yield of the title compound 2.5 g, 69%. Mass Spec (FD) 516. Calculated for C24H16ClF3 N4O2S2 : C, 55.76; H, 3.12; N, 10.84. Found: C, 55.98 H, 3.19; N, 10.78. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC=1N=NC(=CC1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:NC1=CC=C(C=C1)S, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=CC=C(C=C1)SC=1N=NC(=CC1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-Chloro-6-phenylpyridazine (0.026 moles, 5.0 g), 4-aminothiophenol (0.026 moles, 3.3 g) and potassium carbonate (0.026 moles, 3.6 g) were stirred in 250 ml ethanol for 3 days. The reaction was filtered, concentrated, ethyl acetate added, washed with water and dried over sodium sulfate. The solution was concentrated and the product purified by HPLC over silica gel eluted with 50% ethyl acetate/hexane to yield 3-(4-aminophenylthio)-6-phenylpyridazine 6.0 g, 83%. Mass Spec (FD) 279. Calculated for C16H13N3S: C, 68.79; H, 4.69; N, 15.04. Found: C, 68.87; H, 4.43N, 15.31. |
Here is a chemical reaction formula: Reactants are m1_m2:NC1=CC=C(C=C1)SC1=NC=CC=C1, amount is: 0.0 ;m1_m2:ClC1=C(C=C(C=C1)N=C=S)C(F)(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:N1=C(C=CC=C1)SC1=CC=C(C=C1)NC(=S)NC1=CC(=C(C=C1)Cl)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(4-Aminophenylthio)pyridine (6.0 mmoles, 1.2 g) and 4-chloro-3-trifluoromethylphenylisothiocyanate (6.0 mmoles, 1.4 g) were reacted according to procedure C to yield the title compound, 1.9 g, 72%. Mass spec (FD) 439. Calculated for C19H13ClF3N3 S2 : C, 51.88; H, 2.98, N, 9.55 Found: C, 51.99; H, 3.15; N, 9.63. |
Here is a chemical reaction formula: Reactants are m1_m6_m2:NC1=CC=C(C=C1)S, amount is: 0.0 ;m1_m6_m2:[H-].[Na+], amount is: 0.0 MOLE;m3:ClC1=NC=CC=C1, amount is: 0.0 ;m4:NC1=CC=C(C=C1)S, amount is: 0.0 ;m5:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m6_m2:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=CC=C(C=C1)SC1=NC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Aminothiophenol (0.065 moles, 8.1 g) in 275 ml DMF was stirred at room temperature for 1 hr with sodium hydride (0.065 moles previously washed with hexane). 2-Chloropyridine (0.06 moles, 6.8 g) was added and the reaction mixture was stirred for 6 hr. An additional 5.2 g of 4-aminothiophenol was added and the reaction stirred at room temperature for 16 hr. Water was added and the product extracted with ethyl acetate. The solution was washed thoroughly with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 30% ethyl acetate/hexane to yield 2-(4-aminophenylthio)pyridine 1.2 g, 10%. Mass spec (FD) 202. Calculated for C11H10N2S: C, 65.32; H, 4.98, N, 13.85 Found: C, 65.23; H, 5.09; N, 13.63. |
Here is a chemical reaction formula: Reactants are m4:[Cl-].[Na+], amount is: 0.0 MOLE;m1_m2_m3_m5:O=C1CCC2=C(NC=3C=CC=C1C23)C(=O)OCC, amount is: 0.0 ;m1_m2_m3_m5:[BH4-].[Na+], amount is: 0.0 ;m1_m2_m3_m5:C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1CCC2=C(NC=3C=CC=C1C23)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of ethyl 1,3,4,5-tetrahydro-5-oxo-benz[cd]indole-2-carboxylate (0.40 g, 1.64 mmol), sodium borohydride (0.062 g, 1.64 mmol), ethanol (2 ml) and tetrahydrofuran (8 ml) was stirred at 0°-5° C. for 1.5 hours. The reaction mixture was poured into a 5% aqueous sodium chloride solution, followed by extraction with ethyl acetate (three times). The extract solution was washed twice with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=15/85) to obtain ethyl 1,3,4,5-tetrahydro-5-hydroxy-benz[cd]indole-2-carboxylate (0.40 g). |
Here is a chemical reaction formula: Reactants are m3:CI, amount is: 0.0 ;m4:[Cl-].[Na+], amount is: 0.0 MOLE;m1_m2_m5:OC1CCC2=C(N(C=3C=CC=C1C23)C)C(=O)OCC, amount is: 0.0 ;m1_m2_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1CCC2=C(N(C=3C=CC=C1C23)C)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Ethyl 1,3,4,5-tetrahydro-5-hydroxy-1-methyl-benz[cd]indole-2-carboxylate (0.25 g, 0.96 mmol) was added to a suspension of 60% sodium hydride (0.039 g, 0.96 mmol) in tetrahydrofuran (10 ml), followed by stirring at room temperature for 20 minutes. After the reaction mixture was cooled to 0°-5° C., methyl iodide (0.27 g, 1.93 mmol) was added thereto and the resulting mixture was stirred at 0°-5° C. for 1 hour and then at room temperature for 2.5 hours. The reaction mixture was poured into a 5% aqueous sodium chloride solution, followed by extraction with ethyl acetate (twice). The extract solution was washed twice with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98) to obtain ethyl 1,3,4,5-tetrahydro-5-methoxy-1-methyl-benz[cd]indole-2-carboxylate (0.16 g). |
Here is a chemical reaction formula: Reactants are m3:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m1_m2_m4:N1C(=C2C=3C(=CC=CC13)CCC2)C(=O)OCC, amount is: 0.0 ;m1_m2_m4:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1C(=C2C=3C(=CC=CC13)CCC2)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Ethyl 1,3,4,5-tetrahydro-benz[cd]indole-2-carboxylate (0.40 g, 1.74 mmol) was added to a suspension of 60% sodium hydride (0.077 g, 1.92 mmol) in N,N-dimethylformamide (5 ml), followed by stirring at room temperature for 30 minutes. Then, benzyl bromide (0.36 g, 2.09 mmol) was added and the resulting mixture was stirred for 1.5 hours. Thereafter, the same after-treatment as in Reference Example 1 was carried out to obtain an oil of ethyl 1,3,4,5-tetrahydro -1benzyl-benz[cd]indole-2-carboxylate. 1 Hnmr (CDC13) δ: |
Here is a chemical reaction formula: Reactants are m4:[Cl-].[Na+], amount is: 0.0 MOLE;m1_m2_m3_m5:O=C1CCC2=C(NC=3C=CC=C1C23)C(=O)OCC, amount is: 0.0 ;m1_m2_m3_m5:C[O-].[Na+], amount is: 0.0 ;m1_m2_m3_m5:Cl.NC(=N)N, amount is: 0.0 ;m1_m2_m3_m5:CN(C=O)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:NN=CNC(=O)C=1NC=2C=CC=C3C2C1CCC3=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of ethyl 1,3,4,5-tetrahydro-5-oxo-benz[cd]indole-2-carboxylate (1.00 g, 4.11 mmol), sodium methoxide (2.22 g, 41.1 mmol), guanidine hydrochloride (3.92 g, 41.1 mmol) and N,N-dimethylformamide (15 ml) was stirred overnight at room temperature. After completion of the reaction, a 5% aqueous sodium chloride solution was added to the reaction mixture under ice-cooling, followed by extraction with ethyl acetate (three times). The extract solution was washed twice with a 5% aqueous sodium hydrogencarbonate solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=95/5) to obtain N-(aminoiminomethyl) -1,3,4,5-tetrahydro-5-oxo-benz[cd]indole-2-carboxamide (1.00 g). This compound (1.00 g) was treated with a mixture of isopropanol/water and methanesulfonic acid (0.75 g, 7.80 mmol) to obtain crude N-(aminoiminomethyl)-1,3,4,5-tetrahydro-5-oxo-benz[cd]indole-2-carboxamide methanesulfonate. This crude product was recrystallized from methanesulfonic acid (0.04 g, 0.39 mmol) and water (36 ml) to obtain N-(aminoiminomethyl)-1,3,4,5-tetrahydro-5-oxo-benz[cd]indole-2-carboxamide methanesulfonate (0.72 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:CS(=O)(=O)O.NN=CNC(=O)C=1NC=2C=CC=C3C2C1CCC3O, amount is: 0.0 ;m1_m2_m3:CS(=O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NN=CNC(=O)C=1NC=2C=CC=C3C2C1CCC3OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of the N-(aminoiminomethyl)-1,3,4,5-tetrahydro-5-hydroxy-benz[cd]indole-2-carboxamide methanesulfonate (0.13 g, 0.37 mmol) obtained in Example 7, methanesulfonic acid (0.036 g, 0.37 mmol) and methanol (20 ml) was heated under reflux for 2 hours. Subsequently, the reaction mixture was concentrated to a volume of about 5 ml under reduced pressure and a 5% aqueous sodium chloride solution was added to the residue. The resulting mixture was made basic with 28% aqueous ammonia and extracted twice with ethyl acetate, and the extract solution was washed twice with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=96/4) to obtain N-(aminoiminomethyl)-1,3,4,5-tetrahydro-5-methoxy-benz[cd]indole -2-carboxamide (0.11 g). This compound (0.11 g) was treated with a solution of methanesulfonic acid (0.05 g) in tetrahydrofuran (2.5 ml) to obtain N-(aminoimino-methyl)-1,3,4,5-tetrahydro-5-methoxy-benz[cd]indole-2-carboxamide methanesulfonate (0.08 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:OC1CCCC2=C(NC=3C=CC=C1C23)C(=O)OCC, amount is: 0.0 ;m1_m2_m3_m5:C[O-].[Na+], amount is: 0.0 ;m1_m2_m3_m5:Cl.NC(=N)N, amount is: 0.0 ;m1_m2_m3_m5:CN(C=O)C, amount is: 0.0 ;m4:[Cl-].[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:NN=CNC(=O)C=1NC=2C=CC=C3C2C1CCCC3O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of ethyl 3,4,5,6-tetrahydro-6-hydroxy-1-H-cyclohepta[cd]indole-2-carboxylate (0.30 g, 1.16 mmol), sodium methoxide (1.26 g, 23.1 mmol), guanidine hydrochloride (2.22 g, 23.1 mmol) and N,N-dimethylformamide (15 ml) was stirred at room temperature for 3 days. The reaction mixture was poured into a 5% aqueous sodium chloride solution, followed by extraction with ethyl acetate (three times). The extract solution was washed twice with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain crude N-(aminoiminomethyl)-3,4,5,6-tetrahydro-6-hydroxy-1H-cyclohepta [cd]indole-2carboxamide. This crude product was added to a solution of methanesulfonic acid (0.22 g) in tetrahydrofuran (12 ml) and the resulting mixture was stirred at 0°-5° C. The insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. A 5% aqueous sodium chloride solution was added to the thus obtained residue, and the resulting mixture was made basic with 28% aqueous ammonia and extracted twice with ethyl acetate. The extract solution was washed with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=96/4) to obtain N-(aminoiminomethyl)-3,4-dihydro-1H-cyclohepta[cd]indole-2-carboxamide (0.16 g). This compound (0.16 g) was treated with a solution of methanesulfonic acid (0.15 g) in tetrahydrofuran (3.5 ml) to obtain N-(aminoiminomethyl)-3,4-dihydro-1H-cyclohepta[cd]indole-2-carboxamide methanesulfonate (0.11 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:IC=1C=C(C(=O)Cl)C=CC1, amount is: 0.0 ;m1_m3_m2_m4:C1(=CC=CC=C1)[C@@H](N)CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:ClCCl, amount is: 0.0 ;m1_m3_m2_m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:IC=1C=C(C(=O)N[C@@H](CO)C2=CC=CC=C2)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a vigorously stirred solution of 3-iodobenzoyl chloride (16.79 g, 63 mmol) in dichloromethane (300 ml) was rapidly added a solution of (R)-(-)-2-phenylglycinol (8.64 g, 63 mmol) in dichloromethane (50 ml). The reaction mixture was stirred for 3 hours and crude product collected by filtration. Recrystallization from isopropyl alcohol gave (+)-2-(3-iodobenzamido)-2(R)-phenylethan-1-ol as white needles (14.74 g, 64%). |
Here is a chemical reaction formula: Reactants are m3_m5:N(=NC(=O)OCC)C(=O)OCC, amount is: 0.0 ;m1_m2_m4:IC=1C=C(C(=O)N[C@@H](CO)C2=CC=CC=C2)C=CC1, amount is: 0.0 ;m1_m2_m4:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:O1CCCC1, amount is: 0.0 ;m1_m2_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:IC=1C=C(C=CC1)C=1OC[C@H](N1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of (+)-2-(3-iodobenzamido)-2(R)-phenylethan-1-ol (14.70 g, 40 mmol) and triphenylphosphine (13.64 g, 52 mmol) in dry tetrahydrofuran (350 ml) was added dropwise a solution of diethyl azodicarboxylate (10.52 g, 52 mmol) in dry tetrahydrofuran (15 ml). The reaction mixture was stirred for 18 h and volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (1:8) to afford (+)-4,5-dihydro-2-(3-iodophenyl)-4(R)-phenyloxazole (7.81 g, 56%) as a liquid. |
Here is a chemical reaction formula: Reactants are m3:C(=O)(O)[O-].[Na+], amount is: 0.0 ;m4:C[Si](C)(C)N=C=O, amount is: 0.0 ;m1_m5:C(C)(C)(C)OC(=O)N(OC(=O)OC(C)(C)C)CC#CC1=CC(=CC=C1)C=1OC[C@H](N1)C1=CC=CC=C1, amount is: 0.0 ;m2:FC(C(=O)O)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)[C@H]1N=C(OC1)C=1C=C(C=CC1)C#CCN(C(=O)N)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of N,O-di(tert-butoxycarbonyl)-[3-[3-(4,5-dihydro-4(R)-phenyl-oxazol-2-yl)phenyl]-2-propyn-1-yl]hydroxylamine (1.99 g, 4 mmol) in dichloromethane (30 ml) cooled to 0° C. was slowly added trifluoroacetic acid (10 ml). The reaction mixture was allowed to warm to room temperature, stirred an additional 30 min., and then poured into a saturated aqueous NaHCO3 solution (100 ml). The mixture was extracted with dichloromethane (3×30 ml) and the organic phase washed with brine (20 ml), dried (MgSO4) and evaporated. The resulting residue was dissolved in tetrahydrofuran (20 ml) and trimethylsilyl isocyanate (0.84 ml, 6.3 mmol) added. After stirring for 10 min. precipitation of product occurred. Methanol (1 ml) was added and solvent was removed by evaporation. The resulting solids were recrystallized from ethyl acetate to afford the title compound (0.98 g, 72 %) as white solids. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:[Si](C)(C)(C(C)(C)C)OC[C@@H](C1=CC=CC=C1)NC(C1=CC(=CC=C1)I)=O, amount is: 0.0 ;m1_m4_m2:COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC, amount is: 0.0 ;m3:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:COCCOC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC[C@@H](C1=CC=CC=C1)NC(C1=CC(=CC=C1)I)=S, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of N-(1-tert-butyldimethylsilyloxy-2(R)-phenylethan-2-yl)-3-iodobenzamide (13.1 g, 27.2 mmol) in 1,2-dimethoxyethane (80 ml) was added Lawesson's reagent (8.2 g, 20 mmol). The reaction mixture was stirred at ambient temperature for 1 h and then at 60° C. for 2 hours, cooled and poured into water (100 ml). The mixture was extracted with CH2 Cl2 (2×50 ml), washed with brine (100 ml), dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (=1:7) to afford N-(1-tert-butyldimethylsilyloxy-2(R)-phenyl-ethan-2-yl)-3-iodobenzthiamide (4.99 g, 50%) as a yellow liquid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[Si](C)(C)(C(C)(C)C)OC[C@@H](C1=CC=CC=C1)NC(C1=CC(=CC=C1)I)=S, amount is: 0.0 ;m1_m3_m2:[F-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:IC=1C=C(C=CC1)C=1SC[C@H](N1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of N-(1-tert-butyldimethylsilyloxy-2(R)-phenylethan-2-yl)-3-iodobenzthiamide (8.1 g, 16 mmol) in THF (70 ml) was added dropwise tetrabutyl-ammonium fluoride (1M in THF, 21 ml). The reaction mixture was stirred at room temperature for 4 hours, solvent removed by evaporation and the resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate/n-hexane (=1:7) to afford 4,5-dihydro-2-(3-iodophenyl)-4(R)-phenylthiazole (2.46 g, 41%). |
Here is a chemical reaction formula: Reactants are m0_m1_m2:FC1=C(C(=O)Cl)C=CC=C1I, amount is: 0.0 MOLE;m0_m1_m2:IC=1C=C(C=CC1)C=1OC[C@H](N1)C1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC1=C(C=CC=C1I)C=1OC[C@H](N1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4,5-Dihydro-2-(2-fluoro-3-iodophenyl)-4(R)-phenyloxazole was prepared from 2-fluoro-3-iodobenzoyl chloride in a similar manner to that of (+)-4,5-dihydro-2-(3-iodophenyl)-4(R)-phenyloxazole as described in Example 1. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:FC1=C(C=CC=C1I)C=1OC[C@H](N1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m4_m3:C(C#C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:C(C)N(CC)CC, amount is: 0.0 ,Catalysts are m1_m2_m4_m3:Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl, amount is: 0.0 .Products are 0:C1(=CC=CC=C1)[C@H]1N=C(OC1)C=1C(=C(C=CC1)C#CCO)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4,5-dihydro-2-(2-fluoro-3-iodophenyl)-4(R)-phenyloxazole (2.28 g, 6.2 mmol), propargyl alcohol (0.22 g, 12.4 mmol) and bis(triphenylphosphine)-palladium(II) chloride (220 mg, 1.1 mmol) in triethylamine (50 ml), was stirred for 1 h under a nitrogen atmosphere, Cul (420 mg, 2.2 mmol) added and the reaction mixture stirred for a further 16 hours. Insoluble material was removed by filtration and the filtrate concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:14) to afford of 3-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)-2-fluorophenyl]-2-propyn-1-ol (1.41 g, 77%) as off-white solids. |
Here is a chemical reaction formula: Reactants are m4_m6:N(=NC(=O)OCC)C(=O)OCC, amount is: 0.0 ;m1_m2_m3_m5:C1(=CC=CC=C1)[C@H]1N=C(OC1)C=1C(=C(C=CC1)C#CCO)F, amount is: 0.0 ;m1_m2_m3_m5:C(C)(C)(C)OC(=O)NOC(=O)OC(C)(C)C, amount is: 0.0 ;m1_m2_m3_m5:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m6:O1CCCC1, amount is: 0.0 ;m1_m2_m3_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)N(OC(=O)OC(C)(C)C)CC#CC1=C(C(=CC=C1)C=1OC[C@H](N1)C1=CC=CC=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 3-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)-2-fluorophenyl]-2-propyn-1-ol (1.41 g, 4.8 mmol), N,O-bis(tert-butoxycarbonyl)hydroxylamine (1.11 g, 4.8 mmol) and triphenylphosphine (1.63 g, 6.2 mmol) in dry tetrahydrofuran (350 ml) was added dropwise a solution of diethyl azodicarboxylate (1.08 g, 6.2 mmol) in dry tetrahydrofuran (15 ml). The reaction mixture was stirred for 2 hours and volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:10) to afford N,O-di(tert-butoxycarbonyl)-[3-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)-2-fluoro-phenyl]-2-propyn-1-yl]hydroxylamine (1.64 g, 67%) as pale yellow plates. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:BrC=1C=C(C(=O)Cl)C=CC1, amount is: 0.0 ;m1_m3_m2_m4:C1(=CC=CC=C1)[C@@H](N)CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:ClCCl, amount is: 0.0 ;m1_m3_m2_m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=C(C(=O)N[C@@H](CO)C2=CC=CC=C2)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a vigorously stirred solution of 3-bromobenzoyl chloride (13 g, 58 mmol) in dichloromethane (500 ml) was rapidly added a solution of (R)-(-)-2-phenyl-glycinol (10.5 g, 76 mmol) in dichloromethane (50 ml). The reaction mixture was stirred for 3 h and insolubles removed by filtration. Concentration of the filtrate gave 2-(3-bromobenzamido)-2(R)-phenylethan-1-ol as colorless solids (18.5 g, quant). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:BrC=1C=C(C(=O)N[C@@H](CO)C2=CC=CC=C2)C=CC1, amount is: 0.0 ;m1_m2_m4:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m3:N(=NC(=O)OCC)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=C(C=CC1)C=1OC[C@H](N1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 2-(3-bromobenzamido)-2(R)-phenylethan-1-ol (18 g, 56 mmol) and triphenylphosphine (19.2 g, 73 mmol)) in dry tetrahydrofuran (350 ml) cooled to -60° C. was added dropwise diethyl azodicarboxylate (12 ml, 73 mmol). The reaction mixture was allowed to warm to ambient temperature, stirred for 18 h and volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:7) to afford 2-(3-bromophenyl)-4,5-dihydro-4(R)-phenyloxazole (10.9 g, 65%) as a pink liquid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C1=CC=CC=C1)OC=1C=C(C(=O)O)C=CC1, amount is: 0.0 ;m1_m3_m2:S(=O)(Cl)Cl, 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(C1=CC=CC=C1)OC=1C=C(C(=O)Cl)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-benzyloxybenzoic acid (22 g, 96 mmol) in toluene (200 ml) was added dropwise thionyl chloride (14.1 ml, 19 mmol). The reaction mixture was heated at 90° C. for 2 hours, cooled to ambient temperature and volatiles removed under reduced pressure to afford crude 3-benzyloxybenzoyl chloride (32 g, quant.). The crude 3-benzyloxybenzoyl chloride was dissolved in CH2Cl2 and added dropwise over 30 min., to a vigorously stirred solution of (R)-(-)-2-phenylglycinol (15.8 g, 115 mmol) and triethylamine (16 ml, 15 mmol) in CH2Cl2 (200 ml) cooled to 0° C. The reaction mixture was allowed to warm ambient temperature and stirred for overnight. Solvent was removed under reduced pressure and the residue partitioned between ethyl acetate (1 L) and water (1 L). The aqueous layer was separated, extracted with ethyl acetate (2×500ml) and the combined organic phase washed with 1N HCl (500 ml), aqueous 4% NaHCO3 solution (500 ml) and brine (500 ml), dried over MgSO4 and concentrated under reduced pressure to give 2-(3-benzyloxybenzamido)-2(R)-phenylethan-1-ol (29 g, 88%) as pale yellow solids. |
Here is a chemical reaction formula: Reactants are m2_m3_m5:C1(=CC=CC=C1)[C@@H](N)CO, amount is: 0.0 ;m2_m3_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m4:C(C1=CC=CC=C1)OC=1C=C(C(=O)Cl)C=CC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3_m5:C(Cl)Cl, amount is: 0.0 ;m1_m4:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C=C(C(=O)N[C@@H](CO)C2=CC=CC=C2)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-benzyloxybenzoic acid (22 g, 96 mmol) in toluene (200 ml) was added dropwise thionyl chloride (14.1 ml, 19 mmol). The reaction mixture was heated at 90° C. for 2 hours, cooled to ambient temperature and volatiles removed under reduced pressure to afford crude 3-benzyloxybenzoyl chloride (32 g, quant.). The crude 3-benzyloxybenzoyl chloride was dissolved in CH2Cl2 and added dropwise over 30 min., to a vigorously stirred solution of (R)-(-)-2-phenylglycinol (15.8 g, 115 mmol) and triethylamine (16 ml, 15 mmol) in CH2Cl2 (200 ml) cooled to 0° C. The reaction mixture was allowed to warm ambient temperature and stirred for overnight. Solvent was removed under reduced pressure and the residue partitioned between ethyl acetate (1 L) and water (1 L). The aqueous layer was separated, extracted with ethyl acetate (2×500ml) and the combined organic phase washed with 1N HCl (500 ml), aqueous 4% NaHCO3 solution (500 ml) and brine (500 ml), dried over MgSO4 and concentrated under reduced pressure to give 2-(3-benzyloxybenzamido)-2(R)-phenylethan-1-ol (29 g, 88%) as pale yellow solids. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C(C1=CC=CC=C1)OC=1C=C(C(=O)N[C@@H](CO)C2=CC=CC=C2)C=CC1, amount is: 0.0 ;m1_m2_m4:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m3_m5:N(=NC(=O)OC(C)C)C(=O)OC(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:O1CCCC1, amount is: 0.0 ;m3_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C=C(C=CC1)C=1OC[C@H](N1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 2-(3-benzyloxybenzamido)-2(R)-phenylethan-1-ol (29 g, 83 mmol) and triphenylphosphine (28.4 g, 108 mmol) in dry tetrahydrofuran (200 ml) was added dropwise a solution of diisopropyl azodicarboxylate (19.6 ml, 108 mmol) in dry tetrahydrofuran (30 ml). The reaction mixture was stirred for 4 hours and volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:9) to afford 2-(3-benzyloxyphenyl)-4,5-dihydro-4(R)-phenyloxazole (23.5 g, 85%) as pale yellow solids. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)OC=1C=C(C=CC1)C=1OC[C@H](N1)C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)(=O)OCC, amount is: 0.0 ,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 .Products are 0:OC=1C=C(C=CC1)C=1OC[C@H](N1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(3-Benzyloxyphenyl)-4,5-dihydro-4(R)-phenyloxazole (3 g, 8.9 mmol) was dissolved in ethyl acetate (15 ml) and hydrogenolyzed in the presence of 10% palladium-on-charcoal (300 mg). Recrystallization from ethyl acetate/n-hexane gave 4,5-dihydro-2-(3-hydroxyphenyl)-4(R)-phenyloxazole (1.03 g, 48% ) as colorless needles. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:OC=1C=C(C=CC1)C=1OC[C@H](N1)C1=CC=CC=C1, amount is: 0.0 ;m1_m4_m2:[H-].[Na+], amount is: 0.0 ;m3_m5:BrCCO[Si](C)(C)C(C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:CN(C=O)C, amount is: 0.0 ;m3_m5:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OCCOC1=CC(=CC=C1)C=1OC[C@H](N1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 4,5-dihydro-2-(3-hydroxyphenyl)-4(R)-phenyloxazole (3.3 g, 13.8 mmol) in N,N-dimethylformamide (30 ml) was added sodium hydride (60% in mineral oil, 0.62 g, 16 mmol) portionwise over 5 min. at ambient temperature. The mixture was stirred for 1 hour, and then a solution of 2-bromo-1-(tert-butyldimethylsilyloxy)ethane (4.94 g, 21 mmol) in N,N-dimethylformamide (5 ml) was added dropwise over 5 min. and the reaction mixture stayed overnight. The reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml), the aqueous layer was separated, extracted with ethyl acetate (2×50 ml) and the combined organic phase washed with 1N HCl (100 ml), aqueous 4% NaHCO3 solution (100 ml) and brine (100 ml), dried (MgSO4) and evaporated. The resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate/n-hexane (=1:6) to afford 1-(tert-butyldimethylsilyloxy)-2-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)phenoxy]ethane (4.7 g, 86%) as a colorless oil. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[Si](C)(C)(C(C)(C)C)OCCOC1=CC(=CC=C1)C=1OC[C@H](N1)C1=CC=CC=C1, amount is: 0.0 ;m1_m3_m2:[F-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)[C@H]1N=C(OC1)C=1C=C(OCCO)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1-(tert-butyldimethylsilyloxy)-2-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)phenoxy]ethane (4.4 g, 11 mmol) in THF (35 ml) was added dropwise tetrabutylammonium fluoride (1M in THF, 14 ml). The reaction mixture was stirred at room temperature for 45 min., solvent removed by evaporation and the resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate/n-hexane (=1:2) to afford 2-[3-(4,5-dihydro-4(R)-phenyl-oxazol-2-yl)phenoxy]ethan-1-ol (2.8 g, 91%) as a colorless oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:OC=1C=C(C=CC1)C=1OC[C@H](N1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m5:[Si](C)(C)(C(C)(C)C)OC[C@H](C)O, amount is: 0.0 ;m1_m2_m3_m5:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m4_m6:N(=NC(=O)OCC)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:O1CCCC1, amount is: 0.0 ;m4_m6:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC[C@@H](C)OC1=CC(=CC=C1)C=1OC[C@H](N1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 4,5-dihydro-2-(3-hydroxyphenyl)-4(R)-phenyloxazole (5.0 g, 20.9 mmol), 1-(tert-butyldimethylsilyloxy)propan-2(S)-ol (4.76 g, 25 mmol) and triphenylphosphine (6.58 g, 25 mmol) in dry tetrahydrofuran (30 ml) was added dropwise a solution of diethyl azodicarboxylate (3.9 ml, 25 mmol) in dry tetra-hydrofuran (5 ml). The reaction mixture was stirred ambient temperature for 1 h and then ay 50° C. for 5 hours. Volatiles were removed by evaporation and the resulting residue purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:6) to afford 1-(tert-butyldimethylsilyloxy)-2(R)-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)phenoxy]propane (8.7 g, quant.) as a colorless oil. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m3_m6:BrCC(=O)OCC, amount is: 0.0 ;m1_m2_m5:OC=1C=C(C=CC1)C=1OC[C@@H](N1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m6:CN(C)C=O, amount is: 0.0 ;m1_m2_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)[C@@H]1N=C(OC1)C=1C=C(OCC(=O)OCC)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a vigorously stirred mixture of 4,5-dihydro-2-(3-hydroxyphenyl)-4(S)-phenyloxazole (2.04 g, 8.5 mmol) and potassium carbonate (2.36 g, 17 mmol) in DMF (40 ml) was added dropwise over 5 min. a solution of ethyl bromoacetate (1.71 g, 10.2 mmol) in DMF (5 ml) at ambient temperature. The reaction mixture was stirred for 12 h and then poured into water (100 ml). The mixture was extracted with diethyl ether (3×50 ml), and the combined extracts were washed with brine (50 ml), dried (MgSO4) and concentrated under reduced pressure to afford title compound (2.77 g, quant.) as a pale yellow liquid. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m1_m2_m3:C1CCOC1, amount is: 0.0 ;m1_m2_m3:C1(=CC=CC=C1)[C@@H]1N=C(OC1)C=1C=C(OCC(=O)OCC)C=CC1, amount is: 0.0 ;m1_m2_m3:[Li+].[BH4-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)[C@@H]1N=C(OC1)C=1C=C(OCCO)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a THF (40 ml) solution of ethyl 3-(4,5-dihydro-4(S)-phenyloxazol-2-yl)phenoxyacetate (2.77 g, 8.5 mmol) was added LiBH4 (0.37 g, 17 mmol) in one portion. After stirring for 4 h, water (40 ml) was added and the mixture diluted with diethyl ether (40 ml). The aqueous layer was separated and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with 0.5 N aqueous HCl (20 ml), brine (20 ml), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (=2:1) to afford title compound (0.95 g, 40%) as a colorless liquid. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:FC1=C(C=CC=C1)O, amount is: 0.0 ;m1_m2_m5_m3:[Si](C)(C)(C(C)(C)C)Cl, amount is: 101.0 MILLIMOLE;m1_m2_m5_m3:N1C=NC=C1, amount is: 0.0 ;m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5_m3:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC=1C(=C(C=CC1)O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-fluorophenol (10.35 g, 9.2 mmol) and tert-butyldimethylsilyl chloride (101 mmol) in DMF (180 ml) was added imidazole (7.54 g, 110 mmol) in one portion. After stirring for 3 h the reaction mixture was poured into water (300 ml) and extracted with diethyl ether (3×100 ml). The combined extracts were washed with 10% aqueous citric acid (100 ml), brine (100 ml), dried (MgSO4) and concentrated under reduced pressure to afford title compound (20.63 g, quant.) as a colorless liquid. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m2:C(C)(CC)[Li], amount is: 0.0 ;m3:C(=O)=O.C(C)OCC, amount is: 0.0 MOLE;m1_m5:[Si](C)(C)(C(C)(C)C)OC=1C(=C(C=CC1)O)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC=1C(=C(C(=O)O)C=CC1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3-tert-butyldimethylsilyloxy-2-fluorophenol (10.59 g, 46.8 mmol) in THF (150 ml) cooled to -70° C. was added dropwise over 5 min. sec-butyllithium (42 ml, 1.12M in cyclohexane). The reaction mixture was stirred ad -70° C. for 1 h and then poured into a slurry of dry-ice/diethyl ether. Water (200 ml) was added cautiously and the organic layer separated and discarded. The aqueous layer was acidified to pH 2 with concentrated HCl and extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried (MgSO4) and evaporated to afford title compound (7.90 g, 70%) as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:[Si](C)(C)(C(C)(C)C)OC=1C(=C(C(=O)O)C=CC1)F, amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m5:[I-].[Na+], amount is: 0.0 ;m4:C(C1=CC=CC=C1)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m1_m2_m3_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=C(C(=O)OCC2=CC=CC=C2)C=CC1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 3-tert-butyldimethylsilyloxy-2-fluorobenzoic acid (7.74 g, 29 mmol), potassium carbonate (24.0 g, 174 mmol) and sodium iodide (25.9 g, 174 mmol) in DMF (180 ml) was added benzyl chloride (8.33 ml, 72.4 mmol) dropwise over 5 min. After stirring for 2 days the reaction mixture was poured into water (400 ml) and extracted with diethyl ether (3×200 ml). The combined extracts were washed with brine (100 ml), dried (MgSO4) and concentrated under reduced pressure. The crude product obtained was recrystallized from 2-propanol to afford title compound (7.19 g, 74%) as white flakes. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C1=CC=CC=C1)OC=1C(=C(C(=O)OCC2=CC=CC=C2)C=CC1)F, amount is: 0.0 ;m1_m3_m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=C(C(=O)O)C=CC1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of benzyl 3-benzyloxy-2-fluorobenzoate (7.13 g, 21 mmol) in methanol (40 ml) was added an aqueous solution of potassium hydroxide (2.38 g, 42 mmol in 40 ml of water) and the mixture heated at reflux for 30 min. The reaction mixture was cooled, washed with diethyl ether (20 ml) and the ethereal layer was discarded. The aqueous layer was acidified to pH 2 with concentrated HCl and extracted with ethyl acetate (3×40 ml). The combined organic extracts were washed with brine (20 ml), dried (MgSO4) and evaporated to afford title compound (4.83 g, 85%) as white solids. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m1_m5_m2:[Si](C)(C)(C(C)(C)C)OC=1C(=C(C(=O)O)C=CC1)F, amount is: 0.0 ;m1_m5_m2:S(=O)(Cl)Cl, amount is: 0.0 ;m3_m6:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:C1(=CC=CC=C1)C, amount is: 0.0 ;m3_m6:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC=1C(=C(C(=O)NC[C@@H](O)C2=CC=CC=C2)C=CC1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-tert-butyldimethylsilyloxy-2-fluorobenzoic acid (3.3 g, 12 mmol, example 36B) in toluene (30 ml) was added thionyl chloride (1.3 ml, 18 mmol) carefully at ambient temperature. After addition was complete, the reaction mixture was heated at reflux for 40 min, then cooled and concentrated in vacuo. The residual oil was dissolved in CH2Cl2 (20 ml) and added dropwise to a solution of (+)-2-amino-1(S)-phenylethanol (1.7 g, 12 mmol, see A. I. Meyers and J. Slade. J. Org. Chem. 1980, 45, 2785.) and triethylamine (2.0 ml, 15 mmol) in CH2Cl2 (20 ml) cooled to 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred a further 30 min. The mixture was poured into water (100 ml) and extracted with CH2 Cl2 (3×10 ml). The combined organic extracts were washed with saturated aqueous NaHCO3 (100 ml), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (=3:2) to afford title compound (4.6 g, 97%) as a pale yellow liquid. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3_m5:[Si](C)(C)(C(C)(C)C)OC=1C(=C(C(=O)NC[C@@H](O)C2=CC=CC=C2)C=CC1)F, amount is: 0.0 ;m1_m2_m4_m3_m5:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m4_m3_m5:N(=NC(=O)OCC)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3_m5:C1CCOC1, amount is: 0.0 ;m1_m2_m4_m3_m5:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OC=1C(=C(C=CC1)C=1O[C@@H](CN1)C1=CC=CC=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-(3-tert-butyldimethylsilyloxy-2-fluorobenzamido)-1(S)-phenylethanol (4.6 g, 12 mmol) and triphenylphosphine (3.7 g, 14 mmol) in THF (50 ml) was added dropwise a solution of diethyl azodicarboxylate (2.2 ml, 42 mmol) in THF (20 ml). After stirring for 1 h, volatiles were removed by evaporation. The residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (13:1 to 9:1) to afford the title compound (2.2 g, 50%) as a pale yellow liquid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[Si](C)(C)(C(C)(C)C)OC=1C(=C(C=CC1)C=1O[C@@H](CN1)C1=CC=CC=C1)F, amount is: 0.0 ;m1_m3_m2:[F-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C(C=CC=C1O)C=1O[C@@H](CN1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-(3-tert-butyldimethylsilyloxy-2-fluorophenyl)-4,5-dihydro-5(R)-phenyloxazole (2.2 g, 5.8 mmol) in THF (20 ml) was added dropwise tetrabutylammonium fluoride (1M in THF, 7 ml). The reaction mixture was stirred at ambient temperature for 10 min., volatiles removed by evaporation and the resulting residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (3:2) to afford the title compound (1.3 g, 86%) as colorless solids. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5_m4_m6:FC1=C(C=CC=C1O)C=1O[C@@H](CN1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m5_m4_m6:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m5_m4_m6:C(C(=C)C)(=O)OCCO, amount is: 0.0 ;m1_m2_m3_m5_m4_m6:N(=NC(=O)OCC)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5_m4_m6:C1CCOC1, amount is: 0.0 ;m1_m2_m3_m5_m4_m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=C)C)(=O)OCCOC1=C(C(=CC=C1)C=1O[C@@H](CN1)C1=CC=CC=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4,5-dihydro-2-(2-fluoro-3-hydroxyphenyl)-5(R)-phenyloxazol e (0.97 g, 3.8 mmol), triphenylphosphine (1.0 g, 4.0 mmol) and 2-hydroxyethyl methacrylate (0.50 ml, 4.0 mmol) in THF (30 ml) was added dropwise a solution of diethyl azodicarboxylate (0.65 ml, 4.0 mmol) in THF (15 ml). After stirring for 1 day, volatiles were removed by evaporation. The residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (2:1) to afford the title compound (1.2 g, 86%) as a pale yellow liquid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5:O1C(OCC1)C1=C(C=C(C(=C1)OC)OC)C(CCCCC)O, amount is: 0.0 ;m1_m2_m3_m4_m5:O1C(OCC1)C1=C(C=C(C(=C1)OC)OC)C(CCCCC)O, amount is: 0.0 MOLE;m1_m2_m3_m4_m5:N1C=NC=C1, amount is: 0.0 ;m1_m2_m3_m4_m5:C(C)(C)(C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)Cl, amount is: 0.0 ;m1_m2_m3_m4_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC(CC1=C(C=C(C(=C1)OC)OC)C=O)CCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (±)-1-(1,3-dioxolanyl)-2-(1-hydroxy)hexyl-4,5-dimethoxybenzene (Compound 32, 2.2 g, 7.09 mmol), imidazole (0.97 g, 14.19 mmol) and t-butylchlorodiphenylsilane (2.8 mL, 10.64 mmol) in DMF (14 mL) was stirred at 23° C. for 72 hours. The reaction was diluted with Et2O and washed with 1N HCl , H2O and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. Flash column chromatography (silica gel, 5:1 hex/EtOAc) gave 3.52 g (99%) of the title compound wherein absence of the acetal blocking group to give the free aldehyde function was unexpected. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5:ClC(F)F, amount is: 0.0 MOLE;m1_m2_m3_m4_m5:COC1=C(C=C(C=C1)C1CNC(NC1)=O)O, amount is: 0.0 ;m1_m2_m3_m4_m5:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5:O, amount is: 0.0 ;m1_m2_m3_m4_m5:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=C(C=C(C=C1)C1CNC(NC1)=O)OC(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Chlorodifluoromethane was bubbled into a solution of (102 mg, 0.459 mmol, 1.0 eq) of tetrahydro-5-(4-methoxy-3-hydroxyphenyl)-2(1H)-pyrimidinone and 64 mg (1.61 mmol, 3.5 eq) of NaOH in 3 ml of H2O and 3 ml of 1,4-dioxane. After 1 hour at room temperature, the reaction mixture was heated to 60° C. for 1.5 hours. Chlorodifluoromethane was bubbled in continuously. The reaction mixture was cooled to room temperature, poured into 150 ml of H2O and 75 ml of ethyl acetate, extracted twice with ethyl acetate. The ethyl acetate extracts were washed twice with 2N NaOH, once with brine, dried over Na2SO4, and concentrated to yield 13.5 mg of a white solid, which was recrystallized from ethyl acetate-hexane to afford 8.4 mg, 7%, of off-white crystals. M.P.: 215°-216° C. Elemental Analysis: Calc'd for C12 H14N2O3F2 : Calc'd: C, 52.95; H, 5.18; N, 10.29. Found: C, 52.88; H, 4.91; N, 10.13. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5:CC(C)OC(=O)/N=N/C(=O)OC(C)C, amount is: 0.0 ;m1_m2_m3_m4_m5:OC=1C=C(C=CC1OC)C1CNC(NC1)=O, amount is: 0.0 ;m1_m2_m3_m4_m5:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 MOLE;m1_m2_m3_m4_m5:C1(=CC=CC=C1)CCCCO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5:O1CCCC1, amount is: 0.0 ;m6:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)CCCCOC=1C=C(C=CC1OC)C1CNC(NC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Diisopropylazodicarboxylate (1.1 ml, 5.70 mmol, 1.2 eq) was added to a mixture of (1.06 g, 4.75 mmol, 1.0 eq) tetrahydro-5-(3-hydroxy-4-methoxyphenyl)-2(1H)-pyrimidinone, (1.37 g, 5.23 mmol, 1.1 eq) triphenylphosphine, and (714 mg, 4.75 mmol, 1.0 eq) 4-phenyl-1-butanol in 20 ml of anhydrous tetrahydrofuran. After heating to reflux for 18 hours, the reaction mixture was cooled to room temperature, diluted with 350 ml ethyl acetate, washed twice with 1N NaOH, once with H2O, once with brine, dried over Na2SO4, and concentrated to yield an orange solid. Silica gel chromatography eluting with 4% CH3OH--CH2Cl2 yielded 527 mg of a white solid, which was recrystallized from ethyl acetate to afford 480 mg, 29%, of white needles. M.P.: 142°-143° C. Elemental Analysis Calc'd for C21 H26N2O3 : Calc'd: C, 71.17; H, 7.40; N, 7.90. Found: C, 71.12; H, 7.32; N, 7.75. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:[H-].[Na+], amount is: 0.0 ;m1_m2_m3_m4:C12C(CC(CC1)C2)OC=2C=C(C=CC2OC)C2CNC(NC2)=O, amount is: 0.0 ;m1_m2_m3_m4:ClCC1=NC2=CC=CC=C2C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ;m1_m2_m3_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C12C(CC(CC1)C2)OC=2C=C(C=CC2OC)C2CN(C(N(C2)CC2=NC1=CC=CC=C1C=C2)=O)CC2=NC1=CC=CC=C1C=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: NaH (63 mg, 1.58 mmol, 1.0 eq, 60% oil dispersion) was added to a mixture of (0.500 g, 1.58 mmol, 1.0 eq) 5-[3-(bicyclo[2.2.1]hept-2-yloxy)4-methoxyphenyl]tetra-hydro-2(1H)-pyrimidinone and (0.279 g, 1.58 mmol, 1.0 eq) 2-chloromethylquinoline in 12 ml of anhydrous dimethylformamide. After stirring for 18 hours at room temperature, the reaction mixture was diluted with 250 ml of H2O and extracted with ethyl acetate. The ethyl acetate extract was washed once with H2O, once with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on a silica gel column, eluting with 21/2% CH3OH-CH2Cl2 to yield 50 mg of a solid, which was recrystallized from ethyl acetate-hexane to afford 45 mg, 5%, of a white crystalline solid. M.P.: 135°-136° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C1(CCCC1)OC=1C=C(C=CC1OC)C1CC(NC1)=O, amount is: 0.0 MOLE;m1_m2:ClCC1=NC2=CC=C(C=C2C=C1)F, 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:FC=1C=C2C=CC(=NC2=CC1)CN1C(CC(C1)C1=CC(=C(C=C1)OC)OC1CCCC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Reaction of 4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidinone with 2-chloromethyl-6-fluoroquinoline, analogous to the procedure of Example 29, yielded the title compound. M.P.: 65°-68° C. High Resolution Mass Spectra: Calc'd: 434.1983. Found: 434.2005. |
Here is a chemical reaction formula: Reactants are m4:C(C)N(CC)CC, amount is: 0.0 ;m1_m5_m2_m6:CS(=O)C, amount is: 0.0 ;m1_m5_m2_m6:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m3_m7:C12C(CC(CC1)C2)OC=2C=C(C=CC2OC)C(C2SC1=C(N(C2=O)CC2=CC=CC=C2)C=CC=C1)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m6:C(Cl)Cl, amount is: 0.0 ;m1_m5_m2_m6:ClCl, amount is: 0.0 MOLE;m8:C(C)(=O)OCC, amount is: 0.0 ;m3_m7:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C12C(CC(CC1)C2)OC=2C=C(C=CC2OC)C=C2SC1=C(N(C2=O)CC2=CC=CC=C2)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of (87 μl, 1.24 mmol, 2.0 eq) dry dimethylsulfoxide in 3 ml of dry CH2Cl2 at -65° C. was added (0.46 ml, 0.927 mmol, 1.5 eq) of 2.0M oxalyl chloride in CH2 Cl2. The mixture was stirred at ca. -60° C. for 15 minutes, then a solution of (310 mg, 0.618 mmol, 1.0 eq) 2-[[3-(bicyclo[2.2.1]hept-2-yloxy)-4-methoxyphenyl]hydroxy-methyl]-4-(phenylmethyl)-2H-1,4-benzothiazin-3(4H)-one in 10 ml dry CH2Cl2 was added dropwise at -65° C. The mixture was allowed to warm to -30° C. over 1 hour, then cooled to -78° C. and (0.43 ml, 3.09 mmol, 5.0 eq) triethylamine was added to the mixture. The mixture was stirred at room temperature for 1 hour then diluted with 400 ml ethyl acetate, washed twice with H2O, once with brine, dried over MgSO4, and concentrated to give 0.3 g of an oil. Silica gel chromatography eluting with 10% ethyl acetate-hexane gave 120 mg of a yellow oil, which was recrystallized from ether-hexane to yield 55 mg, 18%, of a yellow solid. M.P.: 135°-137° C. Elemental Analysis Calc'd for C30H29NO3S: Calc'd: C, 74.51; H, 6.04; N, 2.90. Found: C, 74.53; H, 5.48; N, 2.88. |
Here is a chemical reaction formula: Reactants are m2:[Li]CCCC, amount is: 0.0 ;m3_m5:CC=1N(C2=C(C=NC=C2)N1)C1=CC=C(C=O)C=C1, amount is: 0.0 MOLE;m3_m5:O1CCCC1, amount is: 0.0 ;m1_m4:[Br-].C1(CCCC1)OC=1C=C(C=CC1OC)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)C=CC1=C(C=CC=C1)C1=NC=CC2=C1N=C(N2)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred suspension of (1.74 g, 3.13 mmol, 1.2 eq) [[3-(cyclopentyloxy)-4-methoxyphenyl]methyl]triphenylphosphonium bromide in 20 ml dry tetrahydrofuran at -50° C. was added (1.1 ml, 2.78 mmol, 1.1 eq) of 2.5M n-BuLi. The mixture was warmed to 0° C. over 1 hour, cooled to -78° C., and a solution of (600 mg, 2.53 mmol, 1.0 eq)-4-(2-methyl-1H-imidazo[4,5-c]pyridin-1-yl)benzaldehyde in 20 ml dry tetrahydrofuran was added dropwise over 10 minutes. The reaction mixture was allowed to warm to room temperature over 18 hours then was quenched with 10 ml saturated NH4Cl solution. The mixture was poured into 200 ml of H2O and extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed once with H2O, once with brine, dried over MgSO4, and concentrated to give 2 g of an oil. Flash chromatography eluting with 65% acetone-hexane gave 403 mg of crude product, which was recrystallized from ether-hexane to yield 305 mg, 36%, of the cis product. The trans product was isolated from the chromatography yielding 476 mg, and crystallized from isopropylether to give 415 mg, 39%. Cis-product M.P.: 123°-125° C. Trans-Product M.P.: 156°-158° C. Elemental Analysis of the cis-product: Calc'd for C27H27N3O2 : Calc'd: C, 76.21; H. 6.40; N, 9.87. Found: C, 76.14; H, 6.34; N. 9.71. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:C1(CCCC1)OC=1C=C(C=CC1OC)C=CC1=CC=C(C=C1)N1C(=NC=2C=NC=CC21)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:O1CCCC1, amount is: 0.0 ;m1_m4_m2_m3:CO, amount is: 0.0 ,Catalysts are m1_m4_m2_m3:[Pd], amount is: 0.0 .Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)CCC1=CC=C(C=C1)N1C(=NC=2C=NC=CC21)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A cis and trans mixture of 1-[4-[2-[3-(cyclopentyloxy)-4-methoxyphenyl]-ethenyl]phenyl]-2-methyl-1H-imidazo[4,5-c]pyridine (300 mg, 0.705 mmol 1.0 eq) and 300 mg of 10% Pd/C in 10 ml of tetrahydrofuran and 10 ml of methanol was placed on a Parr hydrogenation apparatus and shaken under 50 psi H2 at room temperature for 6 hours. The reaction mixture was filtered through celite, concentrated, and chromatographed on a silica gel column eluting with 5% CH3OH-CH2Cl2 to give 230 mg of clear oil. Recrystallization from ether-hexane gave 239 mg, 79%, of white crystals. M.P.: 123°-125° C. Elemental Analysis Calc'd for C27 H28N3O2 : Calc'd: C, 75.85; H, 6.84; N, 9.83. Found: C, 75.83; H, 6.74; N, 9.65. |
Here is a chemical reaction formula: Reactants are m1_m2:COC1=C(C=C(C=O)C=C1)OC1CCCC1, amount is: 0.0 ;m1_m2:Cl.SC1=C(N)C=C(C=C1)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE;m3_m4:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)C=1SC2=C(N1)C=C(C=C2)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of (440 mg, 2 mmoles) 4-methoxy-3-cyclopentyloxy benzaldehyde and (400 mg, 2.1 mmoles) 2-mercapto-5-fluoroaniline hydrochloride was heated on a steam bath for 15 minutes. The resulting thick orange oil was cooled and dissolved in 5 ml of 10% FeCl3 in methanol and allowed to stir overnight. The reaction was diluted with water and extracted with CH2Cl2. The CH2Cl2 layer was dried and evaporated to give 760 mg of crude product which was purified on silica gel with CH2 Cl2 to give 500 mg of product. Recrystallization from isopropanol gave 140 mg of product. M.P.: 96°-97° C. Elemental Analysis Calc'd for C19H18O2NSF : Calc'd: C, 66.45; H, 5.28; N, 4.08. Found: C, 66.44; H. 5.13; N. 4.06. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C1(CCCC1)Br, amount is: 0.0 ;m1_m2_m3_m4:OC=1C=C(C=CC1OC)N1C=NC2=C1C=CC(=C2)C(=O)OC, amount is: 0.0 MOLE;m1_m2_m3_m4:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCC1)C=1C=C(C=CC1OC)N1C=NC2=C1C=CC(=C2)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of (800 mg, 5.3 mmoles) cyclopentyl bromide, (1.6 g, 5.3 mmoles) methyl 1-(3-hydroxy-4-methoxyphenyl)-1H-benzimidazole-5-carboxylate and 251 mg of 50% sodium hydride in 10 ml of dimethylformamide was stirred at 100° C. for 30 minutes. The reaction was cooled, poured onto H2O and extracted with ethyl acetate. The ethyl acetate layer was dried and evaporated to give 2 g of crude product. Purification on silica gel with CH2Cl2 gave 1.1 g of methyl 1-(3-cyclopentyl-4-methoxyphenyl)-1H-benzimidazole-5-carboxylate. M.P.: 129°-131°. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C1(CCCC1)OC=1C=C(C(N)=S)C=CC1OC, amount is: 0.0 ;m1_m2_m3:ClCC=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)C=1SC=CN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 130 mg of 3-cyclopentyloxy-4-methoxybenzthioamide and 100 mg of chloroacetaldehyde in 15 ml of ethanol was heated at reflux for 6 hours. The volatiles were evaporated and the residue purified on silica gel with CH2Cl2 to give 90 mg of product. M.P.: 72°-75° C. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m1_m2_m3_m5:OC=1C=C(C=CC1OC)N1C=NC=2C=NC=CC21, amount is: 0.0 ;m1_m2_m3_m5:C1(CCCC1)Br, amount is: 0.0 ;m1_m2_m3_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)N1C=NC=2C=NC=CC21, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.05 g of 1-(3hydroxy-4-methoxyphenyl)-1H-imidazo[4,5-c]pyridine, 2.5 g of cyclopentylbromide and 665 mg of NaH in 20 ml of DMF was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate, dried to give 1.4 g of crude product. Recrystallization from CH2Cl2 gave 574 mg product. M.P.: 66°-88° C. |
Here is a chemical reaction formula: Reactants are m1_m5_m2:COC1=C(C=C(C=C1)C1=CC=C(C=C1)C(=O)O)OC(CCCC1=CC=CC=C1)C, amount is: 0.0 ;m1_m5_m2:CN(C)C1=NC=CC=C1, amount is: 0.0 ;m4:C1(CCCCC1)N=C=NC1CCCCC1, amount is: 0.0 ;m3:C=1(C(=CC=CC1)S(=O)(=O)N)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C=CC=C1)S(=O)(=O)NC(=O)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)OC(CCCC1=CC=CC=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of acid 4'-methoxy-3'-(1-methyl-4-phenylbutoxy)-(±)[1,1'-biphenyl]-4-carboxylic acid, (0.257 g, 0.658 mmoles) in 10 ml of anhydrous methylene chloride under hydrogen atmosphere was added dimethylamino pyridine (88.46 mg, 0.728 mmoles); o-Toluenesulfonamide (0.122 g, 0.712 mmoles) and dicyclohexylcarbodiimide (0.124 g, 0.6 mmoles) the reaction mixture allowed to stir for 50 hours. The solvent was evaporated and the resulting solid triturated with methylene chloride:ether (~1:1) which lead to precipitation of by-product DCU which was filtered. Concentration of the mother liquor followed by 3 g additional triturations with ethyl acetate/ether (~1:1) caused additional deposit of white solid which was filtered. The clear filtrate was concentrated and purified on a silica gel column using methylene chloride/methanol as eluant (95:5). Concentration of fractions containing desired products gave a total of 0.37 g of white foamy solid. Recrystallization from ethyl acetate/hexane gave 0.208 grams of white solid. M.P.: 97°-100° C. |
Here is a chemical reaction formula: Reactants are m1_m2:COC1=CC=C(C=C1)CCCCOC=1C=C(C=O)C=CC1OC, amount is: 0.0 ;m1_m2:NC=1C=C(C(=O)O)C=CC1N, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:COC1=CC=C(C=C1)CCCCOC=1C=C(C=CC1OC)C1=NC2=C(N1)C=CC(=C2)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-(4-(4-Methoxyphenyl)-butoxy)-4-methoxybenzaldehyde (2.8 g) and 3,4-diaminobenzoic acid (1.4 g) were heated to about 120° C. over 1 hour. The resulting residue was chromatographed on a 5×10 cm pad of silica gel eluting with ether to give 1.4 g of a beige solid which was recrystallized from 20 ml of methanol. M.P. 167°-169° C. MS m/e 450 (M+ +1). Elemental analysis calculated for C26H28 O5N2 : C, 69.62; H, 6.29; N, 6.24. Found: C, 69.72; H. 6.70; N, 5.75. |
Here is a chemical reaction formula: Reactants are m1_m3:CC1=C(C(=O)O)C=CC(=C1)C1=CC(=C(C=C1)OC)OCCCCCC1=CC=CC=C1, amount is: 0.0 ;m1_m3:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m2_m4:Cl.NO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m4:N1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC1=C(C=C(C=C1)C=1C(=C(C(=O)NO)C=CC1)C)OCCCCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-methyl-4-[4-methoxy-3-(5-phenylpentyloxy)phenyl]benzoic acid (0.13 g, 0.32 mmoles) in oxalyl chloride (5 ml) was heated to reflux under nitrogen for about 10 minutes. The solution was concentrated under reduced pressure and the residue dried at about 25° C. (0.05 mm pressure). The residue was then dissolved in dry THF (5 ml) and added slowly to a solution of hydroxylamine hydrochloride (0.022 g, 0.32 mmoles) in pyridine at about 0° C. After stirring at about 25° C. for about 16 hours the volatiles were removed under reduced pressure and the residue was slurried in 1NHCl. The mixture was then extracted with ethyl acetate and the combined organics were washed with water and brine, and dried over MgSO4. Filtration followed by concentration under reduced pressure yielded a beige solid. Recrystallization from isopropyl ether (10 ml) gave 0.055 grams of the title compound as an off-white solid. M.P. 125°-126°C.; analysis calc'd. for C26 H2 gNO4 : C,74.43; H, 6.97; N, 3.34. Found: C, 73.85; H, 6.78; N, 3.34. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC1=C(C=C(C=C1)Br)OC(OC1=C(C=CC(=C1)Br)OC)=O, amount is: 0.0 ;m1_m3_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC1=CC=C(C(=C1)OC)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of (20.7 g, 47.9 mmol, 1.0 eq) bis(2-methoxy-5-bromophenyl)carbonate in 250 ml methanol and 60 ml (120 mmol, 2.5 eq) of 2N NaOH was refluxed for 2 hours. The reaction mixture was cooled to room temperature, concentrated to a volume of ca 100 ml, and poured 1 L of H2O. The pH was adjusted to 2 using 1N HCl. The acidic mixture was transferred to a separatory funnel, and extracted three times with ether. The ether extracts were combined and washed once with H2 O, once with brine, and then dried over anhydrous sodium sulfate. Filtration, concentration and drying afforded 19.0 g of a white solid, which was recrystallized from petroleum ether to yield 17.63 g, 91% yield, of white prisms. |
Here is a chemical reaction formula: Reactants are m1_m4:NC=1C(=NC=CC1)NC1=CC=C(C=C1)O, amount is: 0.0 ;m1_m4:C(CCCC)(=O)OC(CCCC)=O, amount is: 0.0 ;m2:Cl, amount is: 0.0 ;m3:[OH-].[Na+], 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=NC=2C(=NC=CC2)N1C1=CC=C(C=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of (1.0 g, 4.97 mmol, 1.0 eq) 4-[(3-amino-2-pyridinyl)amino]phenol in 25 ml of valeric anhydride was heated to reflux for 8 hours. The reaction mixture was cooled, poured into 150 ml of 0.5N HCl, stirred 10 minutes, and extracted twice with ether. The ether extracts were combined, washed three times with saturated NaHCO3, once with H2O, once with brine, dried over MgSO4, and concentrated to give an oil. The oil was taken up in 100 ml CH3 OH and treated with 60 ml of 2N NaOH and allowed to stir at room temperature for 1 hour. The mixture was concentrated, poured into 200 ml of H2O and washed twice with ether. The aqueous layer was neutralized, and extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed once with H2O, dried over MgSO4, and concentrated to give 0.7 g of a solid. Silica gel chromatography eluting with 10% CH3OH/CH2Cl2 gave 510 mg, 38%, of a solid. M.P.: 268°-2690° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:BrCCC=C, amount is: 0.0 ;m1_m2_m3_m4:FC1=CC=C(C=C1)O, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(OCCC=C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4-bromo-1-butene (4.0 g), 4-fluorophenol (3.0 g), potassium carbonate (3.8 g) and acetone (75 ml) was heated at reflux over 16 hours. The mixture was then concentrated in vacuo, dluted with ether, washed with water followed by 1N sodium hydroxide, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatography on a silica gel column eluting with 25% ethyl acetate-hexane afforded 1.6 g of a colorless oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)O, amount is: 0.0 ;m1_m2_m3_m5:C(C=O)(=O)O, amount is: 0.0 ;m1_m2_m3_m5:O.C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m5:ClCCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)C=1C=C(C2=C(C(C(O2)=O)O)C1)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 212.5 g (1.00 mol) of 2,4-di-tert-butylphenol (97%), 163.0 g (1.10 mol) of 50% aqueous glyoxylic acid and 0.5 g (2.6 mmol) of p-toluenesulfonic acid monohydrate in 300 ml of 1,2-dichloroethane is refluxed under nitrogen for 3.5 hours on a water separator. Afterwards the reaction mixture is concentrated on a vacuum rotary evaporator. The residue is taken up in 800 ml of hexane and washed three times with water. The aqueous phases are separated in the separating funnel and further extracted with 300 ml of hexane. The organic phases are combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. The residue yields 262.3 g (~100%) of analytically pure 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one in the form of a thick yellowish resin (compound (201), Table 2). |
Here is a chemical reaction formula: Reactants are m1_m2_m7_m5:C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)O, amount is: 0.0 ;m1_m2_m7_m5:C(C=O)(=O)O, amount is: 0.0 ;m3:O, amount is: 0.0 MOLE;m4:C(C)(=O)OC(C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m7_m5:ClCCCl, amount is: 0.0 ;m6:COC(C)(C)C, amount is: 0.0 ,Catalysts are m1_m2_m7_m5:O.C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 .Products are 0:C(C)(=O)OC1C(OC2=C1C=C(C=C2C(C)(C)C)C(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 21.2 g (0.10 mol) of 2,4-di-tert-butylphenol (97%), 16.3 g (0.11 mol) of 50% aqueous glyoxylic acid and 0.05 g (0.26 mmol) of p-toluenesulfonic acid monohydrate in 30 ml of 1,2-dichloroethane is refluxed under nitrogen for 3.5 hours on a water separator. Afterwards the reaction mixture is concentrated on a vacuum rotary evaporator. The residue is taken up in 9.9 ml (0.105 mol) of acetic anhydride and the solution is refluxed for 90 minutes. The reaction mixture is then cooled to room temperature, diluted with 100 ml of tert-butyl methyl ether and washed in succession with water and dilute sodium hydrogencarbonate solution. The aqueous phases are separated and extracted with 50 ml of tert-butyl methyl ether. The organic phases are combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. Chromatography of the residue on silica gel with the solvent system dichloromethane/hexane=2:1 yields 28.0 g (92%) of 3-acetoxy-5,7-di-tert-butyl-3H-benzofuran-2-one (compound (206), Table 2) as a thick reddish resin. |