Thionyl Chloride → HCID 19602322, compound

Participants

Reaction Steps

A mixture of 2-(trimethylsilyl)-3-benzothiophenecarboxylic acid (0.8 g, 3.2 mmol), made as in Example 14, and thionyl chloride (6 mL) was refluxed for 2 h. The excess thionyl chloride was removed under reduced pressure. The crude acid chloride was dissolved in 20 mL methylene chloride and added to a mixture of N-isopropylhydroxylamine hydrochloride (0.4 g, 3.6 mmol) and 4 g sodium bicarbonate in 20 mL methylene chloride and 20 mL water at 0° C. The resulting mixture was stirred at RT for 2 h. The organic layer was separated, washed with brine, dried, and concentrated in vacuo. The crude product was chromatographed on a silica gel column with 10% ethyl acetate/hexane to give 0.65 g of the title compound as a yellow solid, a 66.1% yield. m.p. 115-118° C.

Provenance & Evidence