Ammonia → 2-(Chloromethyl)benzenesulfonamide

Participants

Reaction Steps

A solution of ammonia (5.2 ml) in tetrahydrofuran (250 ml) at -70° was contacted rapidly with a solution of 2-(chloromethyl)benzenesulfonyl chloride (21.8 g) in tetrahydrofuran (125 ml). The stirred mixture was allowed to warm to 0° and volatiles were removed under vacuum. The residue was contacted with ethyl acetate and a small volume of water. The organic layer was dried (MgSO4) and evaporated to give 19.8 g of white solid, m.p. 156°-157.5°. Recrystallization from toluene/ethyl acetate gave a sample with m.p. 157°-160°. 1H nmr δ(CD3)2COTMS 8.16-7.35 (m), 6.75 brds), 5.20 (s), 3.08 (s).

Provenance & Evidence