p-Toluidine → 4-Chloro-N-(4-methylphenyl)-3-(trifluoromethyl)benzamide

Participants

Reaction Steps

To a solution of p-toluidine (0.44 g, 4.1 mmol) in 10 ml of CH2Cl2 (pre-cooled to 0° C.) are added Et3N (1.14 ml, 2 eq.) and 4-chloro-3-trifluoromethyl-benzoyl chloride (1 g, 4.1 mmol) in 5 ml of CH2Cl2. The mixture is slowly warmed to room temperature and continued to stir at room temperature for an hour. The mixture is diluted with 50 ml of CH2Cl2, washed with 1N HCl solution, and brine. The organic layer is separated, dried over MgSO4, filtered, and concentrated. The residue is purified by column chromatography (EtOAc/Hexanes, 2:3) to give 1.25 g (97%) of 4-chloro-N-p-tolyl-3-trifluoromethyl-benzamide.

Provenance & Evidence