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Paper | Regular issue | Vol 24, No. 2, 1986, pp.419-422
Published online, 1st January, 1970
DOI: 10.3987/R-1986-02-0419
■ Studies on Reactive Intermediates. Part V. Reaction of Ketene Dimer with Benzimidazole

Mohsen Daneshtalab* and Tetsuzo Kato

*Department of Chemistry, College of Pharmacy, Tehran University, Tehran 14, Iran

Abstract

Reaction of ketene dimer with benzimidazole in neat condition at room temperature, gave rise to 1-[o-(N-acetoacetylamino)phenyl]-3,5-diacetyl-4-hydroxypyridin-2(1H)-one (III), an adduct of one mole of benzimidazole and three moles of ketene dimer. Hydrolysis of compound III with 10 % hydrochloric acid gave the N-deacetoacetylated product (IV). Heatinq of compound III with 80 % sulfuric acid resulted in the formation of 1-(o-aminophenyl)-5-acetyl-4-hydroxypyridin-2(1H)-one (V). The reaction mechanism is discussed.