Dicyclohexylcarbodiimide → HCID 53698851, compound

Participants

Reaction Conditions

Reaction Steps

3-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2pyridinyl-]-2-propenoic acid (10.85 g), 1 g of N-hydroxybenzotriazole, 0.01 g of N,N-dimethylaminopyridine and 8.24 g of dicyclohexylcarbodiimide were stirred for 30 minutes in 100 ml of dimethylformamide. After cooling to 0° C., 4 g of N-aminoimidazolidinone was added and stirring continued for 1 hour at 0° C. and 10 hours at room temperature. The resulting suspension was then heated to 60° C. and filtered. It was again suspended in 50 ml of dimethylformamide and heated to 60° C. and filtered again. The combined filtrates were evaporated at 40° C. (oil vacuo). The oily residue was stirred with 50 ml of water containing 2 g of sodium bicarbonate. After the filtration, the solid was washed with water, acetone and ether. 12.3 g of solid was obtained after drying. It was stirred together with 8 g of p-toluenesulfonic acid in 100 ml of dichloromethane for 1 hour. Filtration yielded 12.98 g of a white solid. This material was suspended in water. Recrystallization from water/dimethylformamide yielded 8.49 g of the title compound, melting point 271° C.

Provenance & Evidence