ChemicalBook CAS DataBase List N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide

N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide synthesis

13synthesis methods

Product Name:N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide
CAS Number:90356-78-8
Molecular formula:C18H14F4N2O2S
Molecular Weight:398.37

371-42-6

N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide epoxide

90357-51-0

N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide

90356-78-8

Example 1 Preparation of N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropanamide: 4-Fluorobenzenethiol (21 g) was dissolved in methanol (65 ml) and cooled to 0°C. 50% aqueous sodium hydroxide solution (14g) was added in batches under stirring. The reaction mixture was stirred at 0°C for 30 min, followed by continued stirring at 25°C for 1 hr. N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl oxirane amide (40 g) was added to the reaction system and the reaction was stirred at room temperature for 2 hours. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, water (100 ml) was added to the mixture and the pH was adjusted to below 7 with concentrated hydrochloric acid. Methanol was removed by distillation under reduced pressure until no methanol was distilled. The resulting suspension was stirred at 5°C for 3 h. The solid product was collected by filtration and washed with water (2 x 40 ml). Finally, the solid was dried under vacuum at 50-60°C to afford the target product N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropanamide 58 g in 98% yield.

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90357-51-0 Synthesis

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Yield:90356-78-8 98%

Reaction Conditions:

Stage #1: 4-Fluorothiophenol;N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamidewith methanol;sodium hydroxide;water at 0 - 25; for 3.5 h;
Stage #2: N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamidewith hydrogenchloride;water at 5; pH=< 7; for 3 h;

Steps:

1 Preparation of N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropanamide

Example 1 Preparation of N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropanamide A solution of 4-fluorobenzenethiol (21g) in methanol (65 ml) was cooled to 0° C. and aqueous 50% sodium hydroxide (14 g) was added portionwise. The mixture was stirred at 0° C. for 30 minutes, then at 25° C. for 1 hour. To the mixture, N-[4-cyano-3-trifluoromethylphenyl]-2-methyloxiranecaboxamide (40 g) was added and the resulting mixture was stirred at room temperature for 2h. The reaction was determined to complete by TLC. Water (100 ml) was added to the mixture, followed by concentrated hydrochloric acid to a pH below 7. The solution was distilled under vacuum until no methanol distilled ceased, and the resulting suspension was stirred at 5° C. for 3 hours. The solid was collected by filtration and rinsed with water (2*40 ml). The solid was dried under vacuum at 50-60° C. to give 58 g (98%) of N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropanamide.

References:

US2007/27211,2007,A1 Location in patent:Page/Page column 2; 4

371-42-6
322 suppliers
$6.00/5g