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

Resumo

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.