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Synthesis of Cyanamides via a One-Pot Oxidation-Cyanation of Primary and Secondary Amines

Nadine Kuhl*, Saurin Raval, Ryan D. Cohen

*Department of Process Research & Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States, Email: nadine.kuhlmerck.com

N. Kuhl, S. Raval, R. D. Cohen, Org. Lett., 2019, 21, 1268-1272.

DOI: 10.1021/acs.orglett.8b04007


Abstract

An operationally simple oxidation-cyanation enables the synthesis of cyanamides using inexpensive and commercially available N-chlorosuccinimide and Zn(CN)2 as reagents. The method avoids the direct handling of toxic cyanogen halides and is amenable for the cyanation of various primary and secondary amines and aniline derivatives.


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Key Words

cyanamides, N-chlorosuccinimide


ID: J54-Y2019