Synlett 2017; 28(12): 1437-1440
DOI: 10.1055/s-0036-1589000
letter
© Georg Thieme Verlag Stuttgart · New York

Direct Introduction of an N,N′-Nonsubstituted Carboxamidine Group by Grignard Addition to Silylated Cyanamide

Thomas Guethner*, Eva Huber, Juergen Sans, Franz Thalhammer
Further Information

Publication History

Received: 26 January 2017

Accepted after revision: 17 March 2017

Publication Date:
19 April 2017 (eFirst)

Abstract

A new, widely applicable method to substitute a halogen atom by a nonsubstituted carboxamidine group is presented. Grignard addition to N,N′-bis-trimethylsilylcarbodiimide gives amidinates, which split off the silyl groups during standard aqueous workup. The corresponding amidines are obtained in high yield with high selectivity. Examples for purification procedures are given.