Iodoethane → 2-(Ethylthio)benzothiazole

Participants

Reaction Steps

2-Mercaptobenzothiazole (16.72 g, 0.1 mol) in 52 ml 95% alcohol was reacted with 10.1 g (0.1 mol) triethylamine to give a brown solution. Iodoethane (15.6 g, 0.1 mol) was added and the mixture refluxed 45 minutes. The mixture was cooled and the solvent removed by rotary evaporation. Water (100 ml) was added to the residue and an oil separated. The aqueous phase was extracted 2×50 ml methylene chloride, the combined organic phases washed with 50 ml water, and then dried over Na2SO4. Filtration and rotary evaporation yielded a brown liquid which was distilled at 140°-141.5° C. (0.15 mm) to give 10.87 g (56%) pale yellow liquid.

Provenance & Evidence