Aminomethylation of Thioureas with  N , N -Dimethyl-1-(triethylsiloxy)methanamine, Involving Amino Group Exchange

J. McMahon; H. K. Sharma; A. Metta-Magaña; K. H. Pannell

doi:10.1134/S1070428019110198

Aminomethylation of Thioureas with N,N-Dimethyl-1-(triethylsiloxy)methanamine, Involving Amino Group Exchange

Authors: McMahon J.¹, Sharma H.K.¹, Metta-Magaña A.¹, Pannell K.H.¹
Affiliations:
1. Department of Chemistry
Issue: Vol 55, No 11 (2019)
Pages: 1764-1771
Section: Article
URL: https://journals.rcsi.science/1070-4280/article/view/221405
DOI: https://doi.org/10.1134/S1070428019110198
ID: 221405

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Abstract

The O-triethylsilylated hemiaminal Et₃SiOCH₂NMe₂ readily transfers the Me₂NCH₂-group to various thioureas under mild conditions and without catalysts or co-reagents. In the reaction with PhNHC(=S)·NHPh, the initially formed mono-substituted derivative PhNHC(=S)NPhCH₂NMe₂ readily rearranges to produce the unsymmetrical thiourea PhNHC(=S)NMe₂ and hexahydro-1,3,5-triphenyl-1,3,5-triazine.