Diethyl Ether → S-benzylthioacetimidate hydrobromide

Participants

Reaction Steps

To a solution of thioacetamide (0.478 g, 6.36 mmol) in CHCl3 (16 mL) was added benzyl bromide (0.76 mL, 6.39 mmol) and the resultant solution was heated to reflux for 2 hours. The mixture was cooled to room temperature. Ether (50 mL) was added and the mixture was cooled in an ice-water bath to precipitate a white solid. The supernatant solution was decanted and the solid was washed with ether (2×50 mL). The solid was dried under vacuum to provide 1.44 g (92%) of S-benzylthioacetimidate hydrobromide as a white solid. 1H NMR (DMSO-d6) δ 2.63 (s, 3H), 4.61 (s, 2H), 7.34–7.46 (m, 5H), 11.89 (br s, 1H).

Provenance & Evidence