Diphenylacetaldehyde → N-(2,2-Diphenylethenyl)-2-hydroxybenzo(b)thiophene-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 2-hydroxybenzo(b)thiophene-3-carboxamide (0.485 g, 0.0025 m), diphenylacetaldehyde (0.51 g, 0.0026 m), p. toluenesulfonic acid hydrate (30 mg), and dried toluene (15 ml) is set in an oil-bath at 100° C., the bath temperature raised to 150° C., and the mixture heated under reflux until thin-layer chromatography of the mixture indicates completeness of reaction. The cooled reaction mixture is concentrated in vacuo and the residue chromatographed on silica gel (v/v 10-50% CH2Cl2 in hexane) to yield N-(2,2-Diphenylethenyl)-2-hydroxybenzo(b)thiophene-3-carboxamide.

Provenance & Evidence