Cyanamide → Metiamide

Participants

Reaction Steps

The compounds of Formula I are also useful as intermediates in the production of cyanoguanidine compounds. For example N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]thiourea may be reacted with a heavy metal salt of cyanamide such as lead cyanamide to yield N-cyano-N'-methyl-N"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine, or N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]thiourea may be alkylated and the resultant isothiourea treated with a strong base and cyanamide to give N-cyano-N'-methyl-N"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine.

Provenance & Evidence