Ammonia → 4-(Trifluoromethyl)-cinnamamide

Participants

Reaction Conditions

Reaction Steps

4-(Trifluoromethyl)cinnamic acid (64.85 g, 300 mmol) was added to toluene (325 ml) and dimethylformamide (2.2 ml). Thionyl chloride (26.3 ml, 361 mmol) was added dropwise at room temperature. The mixture was heated at 45° C. for 2 hours. The obtained reaction mixture was added dropwise to 25% aqueous ammonia (325 ml) while keeping the mixture at 5-20° C. The mixture was stirred at room temperature for 1 hour. The crystals were filtered, washed with water and isopropyl ether and dried under reduced pressure to give 4-(trifluoromethyl)-cinnamamide (60.76 g, yield 94%). H-NMR (CDCl3-DMSO-d6, δ, 300 MHz) 5.93(1H,s), 6.53(1H,d,J=15.8 Hz), 6.75(1H,s), 7.48-7.53(5H,m).

Provenance & Evidence