Hydrochloric Acid → HCID 19817731, compound

Participants

Reaction Steps

A solution of sodium nitrite (0.79 g) in water (5 ml) was added dropwise to a mixture of 4'-amino-2'-(2,4-difluorobenzyl)methanesulfonanilide (3.0 g) and hydrochloric acid (1.7 ml) in water (15 ml) at 0° to 5° C., and the solution was stirred for 20 minutes at the same temperature. The resulting solution was added dropwise to a mixture of sodium cyanide (1.7 g) and cupric sulfate pentahydrate (3.1 g) in water (25 ml) at 5 to 10° C. N,N-Dimethylformamide (30 ml) was added and the mixture was adjusted to pH 7 with sodium bicarbonate. The mixture was stirred at room temperature for 1 hour and at 60° C. for 4 hours. The reaction mixture was poured into ice-water (200 ml) and extracted with ethyl acetate. The organic layer was washed with water, dried and evaporated. The residue (2.6 g) was purified by column chromatography on silica gel (80 g) eluting with a mixture of toluene and ethyl acetate (5:1) followed by recrystallization from ethanol to give prisms of 4'-cyano-2'-(2,4-difluoro-α-hydroxybenzyl)methanesulfonanilide (1.1 g).

Provenance & Evidence