3-(Trifluoromethyl)aniline → HCID 19354604, compound

Participants

Reaction Steps

To a stirred suspension of 2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoic acid (0.70g) in dichloromethane was added oxalylchloride (0.22 ml) followed by 1 drop of dimethylformamide. The reaction mixture was stirred at ambient temperature for 30 minutes and then cooled to 0° C. To the solution was added in turn triethylamine (0.36 ml), 3-aminobenzotrifluoride (0.34 g) and then triethylamine (0.36 ml). The reaction mixture was stirred at 0° C. for 30 minutes and at ambient temperature for 2 hours then washed in turn with water, 2M hydrochloric acid, water, 1M sodium carbonate and water. The organic solution was dried (magnesium sulphate) and evaporated under reduced pressure to give N-(3-trifluoromethylphenyl)-2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 2, 0.25 g) as a beige solid, m.p. 58-60° C.

Provenance & Evidence