Benzoyl Peroxide → N-(4-chlorophenyl)-2-[((5-(bromomethyl)-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide

Participants

Reaction Steps

To a suspension of N-(4-chlorophenyl)-2-[((5-methyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide (2.6 g, 6.0 mmol) in dry benzene (250 mL) were added N-bromosuccinimide (1.2 g, 6.6 mmol) and benzoyl peroxide (0.15 g, 0.6 mmol). The mixture was refluxed while irradiating with a 250 Watt lamp. After 28 hours the reaction was concentrated of all volatiles in vacuo and the resulting solid triturated with benzene. Purification by flash chromatography on silica gel afforded 2.3 g (75% yield) of N-(4-chlorophenyl)-2-[((5-bromomethyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide as a white solid; NMR (DMSO-d6) 11.1 (s, 1), 10.7 (s, 1), 8.3 (d, 1), 7.9 (s, 1), 7.7 (d, 2), 7.6 (d, 1), 7.4 (d, 2), 7.3 (s, 1), 4.9 (s, 2) ppm.

Provenance & Evidence