2-Methylbenzenesulfonamide → 4-Tert-butyl-2-{5-[2-(2-methylbenzenesulfonamidocarbonyl)phenylmethoxy]benzofuran-2-yl}thiazole

Participants

Reaction Steps

A solution of 4-tert-butyl-2-[5-(2-carboxyphenylmethoxy)benzofuran-2-yl]thiazole (0.2 g), 2-methylbenzenesulfonamide (0.11 g), 4-dimethylaminopyridine (0.12 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.19 g) in N,N-dimethylformamide (10 ml) was stirred at ambient temperature for 1 day. The resulting mixture was poured into ice-water. The resulting precipitates were collected by filtration and washed with water. The crude compound was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol (40:1). The fractions containing object compound were combined and concentrated under reduced pressure to give an oil. The oil was crystallized with ethanol and filtered to give 4-tert-butyl-2-{5-[2-(2-methylbenzenesulfonamidocarbonyl)phenylmethoxy]benzofuran-2-yl}thiazole (0.28 g).

Provenance & Evidence