Hydrochloric Acid → Methyl 3-[({2-[(diaminomethylidene)amino]-1,3-thiazol-4-yl}methyl)sulfanyl]propanimidate

Participants

Reaction Conditions

Reaction Steps

3-(2-Guanidino-4-thiazolylmethylthio)propionitrile (12.82 g) was dissolved in a mixture of dry methanol (75 ml) and dry chloroform (150 ml) and the stirred solution was cooled (under nitrogen) in an ice-salt bath to 2° C. Hydrogen chloride gas (dried) was passed through the solution for three hours, keeping the temperature at 0°-10° C. The solution was then allowed to stand in a stoppered flask at ca 0° C. for 20 hours. The solvents were removed at reduced pressure and the oily residue added to ice-water (200 ml) containing potassium carbonate (30 g). The mixture was extracted with chloroform containing 20% methanol (4×150 ml) and the combined organic extracts were dried (MgSO4). The solvent was removed to give methyl 3-(2-guanidino-4thiazolylmethylthio)propionimidate (13.60 g) as a tacky light-brown oil.

Provenance & Evidence