Dimethylformamide → HCID 22473695, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.6 M solution in hexanes; 6.25 ml) was added dropwise under nitrogen at −70° C. to a stirred solution of 3-(benzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole (2.58 g) in tetrahydrofuran (40 ml), then the mixture was stirred at −70° C. for 10 minutes and at 0° C. for 35 minutes. Dimethylformamide (0.85 ml) was added, the mixture was stirred at 0° C. for 1.5 hours, then it was poured into saturated aqueous ammonium chloride solution (200 ml). The product was extracted into ethyl acetate (2×200 ml), then the combined extracts were washed with water (2×100 ml) and 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 19:1 mixture of ethyl acetate and methanol as eluant. Appropriate fractions were combined and the solvents were removed in vacuo to give 3-(benzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazole-2-carboxaldehyde (0.73 g) as a yellow solid which was used without further purification.

Provenance & Evidence