Cyanamide → N,N'-dicyano-N"-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine

Participants

Reaction Steps

To a solution of sodium metal (1.01 g) in ethanol (120 ml) were added cyanamide (18.5 g) and N-cyano-S-methyl-N'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]isothiourea (10.76 g). The resulting mixture was heated under reflux for 1.5 hrs. After concentration under a reduced pressure, the residue was added to cold water (50 ml) and acidified (pH 4.5) with 10% HCl and cooled for 1 hr. in an ice bath. The precipitate was filtered, washed with water and dried. The resulting crude product (7.43 g) was recrystallized from C2H5OH-H2O (1:1) to give N,N'-dicyano-N"-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine (5.17 g).

Provenance & Evidence