Acetonitrile → N,N-bis(2-oxiranylmethyl)benzenesulfonamide

Participants

Reaction Steps

This reaction is very exothermic so care must be taken if the reaction is scaled up. Acetonitrile (400 mL) and (+)-epichlorohydrin (100 mL, 118.3 g, 0.78 mol) were added to benzenesulfonamide (50.0 g, 0.32 mol), followed by cesium carbonate (228 g, 0.70 mol). The mixture was heated at reflux for 15 hours with mechanical stirring. After cooling to room temperature water was added (250 mL) and the organic phase separated and concentrated under reduced pressure. The residual oil was chromatographed over silica (300 g), eluting with dichloromethane (1 L) and then dichloromethane:ethyl acetate (3 L of 19:1), to give the sub-title compound as an oil (39.4 g, 46%).

Provenance & Evidence