Triethylamine → HCID 54570443, compound

Participants

Reaction Steps

To a solution of 2-cyano-2-(1-ethoxycarbonyl-1-methylethoxyimino)acetamidine acetate (685 g) in methanol (6.85 l) was added triethylamine (557 g) at -13°~-15° C. over a 20-minute period and then bromine (344 g) was added thereto at the same temperature over the same period. The solution was stirred at -13°~-15° C. for 15 minutes, then N,N-dimethylformamide (685 ml) was added to the solution at the same temperature, and a solution of potassium thiocyanate (209 g) in methanol (2.09 l) was added thereto at -13°~-15° C. over a 30-minute period. After being stirred at -5°~0° C. for an hour, the solution was poured into a cold water (5°~10° C.) and stirred for an hour under ice-cooling. The resulting precipitates were collected by filtration, washed with cold water and dried to give 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-ethoxycarbonyl- 1-methylethoxyimino)acetonitrile (390 g).

Provenance & Evidence