Thionyl Chloride → 2-(2-Chloroethylthio)-1-methylimidazole hydrochloride

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (1.41 ml, 19 mmol) was slowly added to a solution of 2-(2-hydroxyethylthio)-1-methylimidazole (1.81 g, 11 mmol) in trichloromethane (20 ml) at 5° C. The mixture was stirred for 1 hour at 5° C. and then for 3 hours at ambient temperature. The volatiles were removed by evaporation and the residue azeotroped with toluene to give 2-(2-chloroethylthio)-1-methylimidazole hydrochloride (1.5 g, 77%). 1H NMR Spectrum: (DMSOd6) 3.58 (t, 2H); 3.78(s, 3H); 3.80(t, 2H); 7.78(d, 1H); 7.83(d, 1H)

Provenance & Evidence