Hydrochloric Acid → N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylprop-2-enamide

Participants

Reaction Conditions

Reaction Steps

To a solution of methacrylamide (153.00 g, 1797.88 mmol) in 800 mL of N,N-dimethylformamide was added 4-cyano-3-(trifluoromethyl)phenyl fluoride (200 g, 1057.58 mmol) at room temperature. The solution was cooled in a methanol/dry ice bath to −20° C. To this cooled solution was added sodium hydride (102 g, 2696.84 mmol), portion-wise, while keeping the reaction mixture temperature below 70° C. The reaction mixture was allowed to cool to room temperature and stirred for 4 hours under nitrogen atmosphere. Water (915 mL) was added followed by 18% HCl (250 mL) and hexane (970 mL). The resultant slurry was allowed to stir overnight. The solid was filtered, washed sequentially with water (3×150 mL) and hexane (100 mL), and dried at 60° C. to give the title product as an off white solid (260 g, 97%).

Provenance & Evidence