Toluene → 4-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride

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Reaction Conditions

Reaction Steps

4-Bromo-N-(4-chloro-phenyl)-benzimidoyl chloride is prepared by heating 4-bromo-N-(4-chloro-phenyl)-benzamide (13.39 g, 43.2 mmol) and thionyl chloride (100 mL) for 1 h. The clear solution is concentrated and the residue obtained is coevaporated with toluene (100 mL). A solution of 5-amino-1-(3-nitro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester (1, 4.00 g, 14.4 mmol) in dry chloroform (50 mL) is then added and the resulting mixture is concentrated to afford a dry residue. It is heated to 170° C. with out solvent for 6 h. The crude product obtained is purified by column chromatography to afford the product as greenish black solid as product (6).

Provenance & Evidence