Ammonia → 3-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)propanimidamide hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)propanenitrile (20.0 g, 61.4 mmol) in toluene (30 mL) and methanol (30 mL) was added dropwise acetyl chloride (18.8 g, 239 mmol) over 5 min at 0° C. under N2. The reaction mixture was stirred at 25° C. for 8 h, then concentrated. It was dissolved with toluene (5 mL), cooled to 0° C. in an ice-bath, slowly mixed with ammonia (30.0 mL, 210 mmol), stirred at 25° C. overnight, filtered, washed with toluene/methanol (1/1) and concentrated. Purification via recrystallization with diethyl ether (50 mL) then afforded the title compound as a white solid (5.4 g, 25.7%).

Provenance & Evidence