Diethyl Ether → S-benzylthioacetimidate hydrobromide
Reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].[CH2:5]([Br:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCOCC>C(Cl)(Cl)Cl>[BrH:12].[CH2:5]([S:3][C:1](=[NH:4])[CH3:2])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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).