Ammonia → 3-(4-(4-Fluorophenoxy)phenyl)propanimidamide

Participants

Reaction Steps

To a solution of 3-(4-(4-fluorophenoxy)phenyl)propanenitrile (4.4 g, 18.24 mmol) in toluene (25 mL) and methanol (5.94 mL) was added dropwise AcCl (6.48 mL, 91 mmol) at 0° C. in 5 min. The mixture was stirred at room temperature for 2 h. The mixture was cooled to 0° C. in an ice bath, and ammonia (26.1 mL, 182 mmol) in methanol was added dropwise in 5 min. The mixture was stirred at room temperature overnight. The mixture was filtered to remove the solid, and the solid was washed with toluene (40 mL) and methanol (40 mL). The combined filtrate was concentrated in vacuo, the residue was triturated with diethyl ether, the resulting white solid was collected by filtration, washed with diethyl ether and dried in vacuo to afford the title compound (5.4 g, 16.12 mmol, 88% yield) as white solid. LCMS: rt=1.03 min, [M+H+]=259

Provenance & Evidence