Wang You
2007
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Journal
Journal of Beijing University of Chemical Technology
Abstract
1-Adamantanecarboxylic acid has been synthesized by the reaction of adamantane with HCOOH in the presence of H2SO4,and subsequently converted to 1-adamantoyl chloride by refluxing with SOCl2 for 1 h.Finally,reaction of 4-chloroaniline with 1-adamantoyl chloride afforded N-(4-chlorophenyl)-1-admantanecarboxamide,an important bifunctional pharmaceutical intermediate.The overall yield was 83.3%.The product was characterized by IR and 1H-NMR spectroscopy and the effect on the yield of using solvents with different polarity such as acetonitrile,acetone,dichloroethane,and toluene in the amidation step was investigated.The results showed that the yield increased with decreasing solvent polarity.