Dimethyl Disulfide → HCID 10268863, compound

Participants

Reaction Conditions

Reaction Steps

3-(Benzo[b]thiophen-4-yl)-2-bromo-5,6-dihydroimidazo[2,1-b]thiazole hydrobromide (15 g; prepared in a manner similar to that described in Example 22) was added in portions under nitrogen at 0-5° C. over 20 minutes to a stirred solution of ethylmagnesium chloride (2M solution in ether; 45 ml) in tetrahydrofuran (225 ml), then the mixture was stirred at 0-5° C. for 2 hours. The mixture was cooled to 0° C. and dimethyl disulphide (5.4 ml) was added, then the mixture was stirred at ambient temperature for 18 hours and quenched by the addition of saturated aqueous ammonium chloride solution (150 ml). The majority of the tetrahydrofuran was removed in vacuo, the residue was diluted with water (200 ml) and the product was extracted into ethyl acetate (400 ml). The extract was washed with water (300 ml) and saturated aqueous sodium chloride solution (2×150 ml), then it was dried (Na2SO4), and the solvents were removed in vacuo. The residue was purified by Biotage 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 to leave 3-(benzo[b]thiophen-4-yl)-2-(methylthio)-5,6-dihydroimidazo[2,1-b]thiazole (7.3 g) as a pale yellow solid, m.p. 104-107° C.

Provenance & Evidence