5-Fluorouracil → 1,3-Dibenzoyl-5-fluoropyrimidine-2,4(1H,3H)-dione

Participants

Reaction Conditions

Reaction Steps

2.6 g (0.02 mole) of 5-fluorouracil was suspended in 10 ml of absolute pyridine, and the suspension was stirred at 70° C to form a solution. 17 g (0.12 mole) of benzoyl chloride was added dropwise to the resulting solution followed by heating to 80° C for 1.5 hours while stirring. After completion of the reaction, the reaction mixture was concentrated under reduced pressure (25 mm Hg) to half its original volume, and 50 ml of ethyl acetate was added thereto. After the insoluble matter in the ethyl acetate was removed, the solution was washed twice with water, and dried over Glauber's salt, and the ethyl acetate removed therefrom under reduced pressure (25 mm Hg). Ethanol was then added to the residue, and the mixture heated to 80° C to form a solution followed by allowing the resulting solution to cool to precipitate crystals, which were then filtered to obtain 3.4 g of 1,3-di-N-benzoyl-5-fluorouracil in a yield of 51%.

Provenance & Evidence