Hydrochloric Acid → (S)-oxiranylmethyl methanesulfonamide

Participants

Reaction Steps

To a cold solution of methanesulfonamide (10 g, 0.105 mol) in water (100 mL) in an ice bath was added sodium hydroxide as pellets (8.4 g, 0.21 mol) and then (S)-2-chloromethyloxirane (12.4 g, 0.158 mol). The mixture was stirred at the same temperature for 2 h, and at room temperature for 12 h and then concentrated hydrochloric acid (18 mL) was added. The product was isolated by extracting the aqueous layer with dichloromethane (2×300 mL). The organic layer was dried over MgSO4 and then evaporated to dryness, yielding a colorless liquid (2.5 g), which was used directly in the next step.

Provenance & Evidence