4-氯苯甲醛肟

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 31 g (0.2 mol) of 4-chlorobenzaldoxime was suspended in 200 g of chloroform and chlorine gas was bubbled through the suspension while maintaining the reaction mixture at a temperature of from 5° to 10° C. 3-Chlorobenzaldoxime went into solution while showing a green color upon reaction with chlorine to give a reaction mixture having a deep green color. The reaction mixture turned pale yellowish-brown upon standing; chloroform was then removed from the reaction mixture by distillation under reduced pressure to give 36 g of pale yellowish-brown crystals having a melting point of 75°-80° C. Yield, about 95%. chlorine gas was bubbled through the suspension while maintaining the reaction mixture at a temperature of from 5° to 10° C upon reaction with chlorine to give a reaction mixture chloroform was then removed from the reaction mixture by distillation under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Preparation is carried out as in Example 1 from 23.34 g of 4-chlorobenzaldoxime, 22 g of N-chlorosuccinimide, 29.5 g of diethyl allylphosphonate and 22.9 ml of triethylamine in dichloromethane and provides 52 g of oily product. Preparation

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Preparation is carried out as in Example 1 from 23.34 g of 4-chlorobenzaldoxime, 22 g of N-chlorosuccinimide, 29.5 g of diethyl allylphosphonate and 22.9 ml of triethylamine in dichloromethane and provides 52 g of oily product. Preparation

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound is prepared in analogy to Example 1 from 23.34 g (0.15 mol) of 4-chlorobenzaldoxime, 22 g of N-chlorosuccinimide, 27.1 g of diethyl vinylphosphonate and 22.9 ml of triethylamine, resulting in 49 g of oily product.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 31 g (0.2 mol) of 4-chlorobenzaldoxime was suspended in 200 g of chloroform and chlorine gas was bubbled through the suspension while maintaining the reaction mixture at a temperature of from 5° to 10°C. 3-Chlorobenzaldoxime went into solution while showing a green color upon reaction with chlorine to give a reaction mixture having a deep green color. The reaction mixture turned pale yellowish-brown upon standing; chloroform was then removed from the reaction mixture by distillation under reduced pressure to give 36 g of pale yellowish-brown crystals having a melting point of 75°-80°C. Yield, about 95%. chlorine gas was bubbled through the suspension while maintaining the reaction mixture at a temperature of from 5° to 10°C upon reaction with chlorine to give a reaction mixture chloroform was then removed from the reaction mixture by distillation under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-Chloro-benzaldehyde oxime (6.64 g, 42.70 mmol) and N-chlorosuccinimide (“NCS”) (5.70 g, 42.70 mmol) were dissolved in N,N-dimethylformamide (40 ml). The reaction mixture was stirred at ambient temperature for 90 minutes. A solution of 3-amino-4-cyano-N-[2,6-dimethyl-4-(1-trifluoromethyl-vinyl)-phenyl]-benzamide (4.4 g, 12.20 mmol) (Example I5) and triethylamine (5.95 mL, 0.66 mmol) in N,N-dimethylformamide (40 ml) was added and the reaction mixture was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with water (500 ml) and ethyl acetate (500 ml) and the phases were separated. The organic phase was washed twice with water and the aqueous phases were extracted once with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to give 3-amino-N-{4-[3-(4-chloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-yl]-2,6-dimethyl-phenyl}-4-cyano-benzamide (3.67 g, 59% yield). LC/MS (Method A): 513 (MH+); RT: 2.04. 1H-NMR (CDCl3, 400 MHz): 7.62 (m, 3H), 7.45 (d, 1H), 7.40 (m, 2H), 7.36 (s, 2H), 7.31 (s, 1H), 7.18 (d, 1H), 4.63 (s, 2H), 4.08 (d, 1H), 3.76 (d, 1H), 2.30 (s, 6H) ppm. the reaction mixture was stirred at ambient temperature for 18 hours the phases were separated The organic phase was washed twice with water the aqueous phases were extracted once with ethyl acetate The combined organic phases were dried over sodium sulfate concentrated The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-Chloro-benzaldehyde oxime (6.64 g, 42.70 mmol) and N-chlorosuccinimide (“NCS”) (5.70 g, 42.70 mmol) were dissolved in N,N-dimethylformamide (40 ml). The reaction mixture was stirred at ambient temperature for 90 minutes. A solution of 3-amino-4-cyano-N-[2,6-dimethyl-4-(1-trifluoromethyl-vinyl)-phenyl]-benzamide (4.4 g, 12.20 mmol) (Example I5) and triethylamine (5.95 mL, 0.66 mmol) in N,N-dimethylformamide (40 ml) was added and the reaction mixture was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with water (500 ml) and ethyl acetate (500 ml) and the phases were separated. The organic phase was washed twice with water and the aqueous phases were extracted once with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to give 3-amino-N-{4-[3-(4-chloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-yl]-2,6-dimethyl-phenyl}-4-cyano-benzamide (3.67 g, 59% yield). LC/MS (Method A): 513 (MH+); RT: 2.04. 1H-NMR (CDCl3, 400 MHz): 7.62 (m, 3H), 7.45 (d, 1H), 7.40 (m, 2H), 7.36 (s, 2H), 7.31 (s, 1H), 7.18 (d, 1H), 4.63 (s, 2H), 4.08 (d, 1H), 3.76 (d, 1H), 2.30 (s, 6H) ppm. the reaction mixture was stirred at ambient temperature for 18 hours the phases were separated The organic phase was washed twice with water the aqueous phases were extracted once with ethyl acetate The combined organic phases were dried over sodium sulfate concentrated The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1)