Potassium Carbobenzyloxycyanamide: An Efficient Reagent for Amine Guanylation

Product #L499994

Figure 1. Structure of potassium carbobenzyloxycyanamide

The reaction of amines with an activated carbodiimide represents a powerful method for the preparation of guanidines. A simple and efficient one-pot method for the synthesis of mono-protected guanidines is presented in Scheme 1. Treatment of this cyanamide with trimethylsilyl chloride generates a reactive N-silylcarbodiimide capable of guanylating a variety of amines. Typically the reaction is complete in 5 minutes for primary and secondary aliphatic amines at room temperature. Anilines are also reactive but require a little more time.

Scheme 1. Applications of potassium benzyloxycarbonylcyanamide

Examples of Amine Guanylation with Potassium Carbobenzyloxycyanamide

Reference:

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