Dimethyl Disulfide → HCID 10268862, compound

Participants

Reaction Conditions

Reaction Steps

3-(Benzo[b]thiophen-4-yl)-2-bromo-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (2.3 g) was added in portions under nitrogen at 0-5° C. over 20 minutes to a stirred solution of ethylmagnesium chloride (2.0 M solution in ether; 6.9 ml) in tetrahydrofuran (35 ml), then the mixture was stirred at 0-5° C. for 20 minutes and at ambient temperature 70 minutes. The mixture was cooled to 0° C. and dimethyl disulphide (0.82 ml) was added, then the mixture was stirred at ambient temperature for 4 hours and quenched by the addition of saturated aqueous ammonium chloride solution (40 ml) and water (50 ml). The product was extracted into ethyl acetate (250 ml), then the extract was washed with saturated aqueous sodium chloride solution (2×100 ml), dried (Na2SO4), and the solvents were removed in vacuo. The residue was purified by flash chromatography over silica using a 96:4 mixture of ethyl acetate and methanol as eluant. Appropriate fractions were combined and the solvents removed in vacuo. The residue was triturated with 2M ethereal hydrogen chloride solution (20 ml) and the resulting solid was collected by filtration, washed with ether (2×20 ml) and dried in vacuo to give 3-(benzo[b]thiophen-4-yl)-2-(methylthio)-5,6-dihydroimidazo[2,1-b]thiazole hydrochloride (0.219 g) as a cream solid, m.p. 95-105° C.

Provenance & Evidence