Dimethyl N-cyanodithioiminocarbonate → N-cyano-N'[2-(2-pyridylmethylthio)ethyl]-S-methylisothiourea

Participants

Reaction Steps

A solution of 2-[(2-pyridyl)methylthio]ethylamine (from the dihydrobromide, 20.0 g; 60.6 mmoles) and dimethyl cyanodithioimidocarbonate [prepared according to the procedure described in J. Org. Chem., 32, 1566 (1967)] (8.86 g; 60.6 mmoles) in methanol (150 ml) was stirred at ambient temperature under a positive pressure of nitrogen for 16 hours and then a reflux temperature for 0.5 hours to complete the reaction. The reaction mixture was evaporated under reduced pressure and the crude product was recrystallized from acetonitrile to give N-cyano-N'-{2-[(2-pyridyl)methylthio]ethyl}-S-methylisothiourea; mp 85°-86.5°.

Provenance & Evidence