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Chlorotrimethylsilane Activation of Acylcyanamides for the Synthesis of Mono-N-acylguanidines

Ryan E. Looper*, Travis J. Haussener and James B. C. Mack

*Department of Chemistry, University of Utah, 315 South 1400 East, Salt lake City, Utah 84112, United States, Email:

R. E. Looper, T. J. Haussener, J. B. C. Mack, J. Org. Chem., 2011, 76, 6967-6971.

DOI: 10.1021/jo201264j


Treatment of an acylcyanamide with chlorotrimethylsilane generates a reactive N-silylcarbodiimide capable of guanylating a variety of amines. Typically the reaction is complete in 15 min for primary and secondary aliphatic amines at room temperature. Hindered amines and anilines are also competent nucleophiles but require extended reaction times.

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ID: J42-Y2011-2340