Phenylurea → HCID 14155746, compound

Participants

Reaction Steps

A mixture of 4.57 g (0.036 mole) of 3,3-dimethylglutaraldehyde, 0.20 g (0.001 mole) of p-toluenesulfonic acid monohydrate and 8.64 g (0.072 mole) of anhydrous magnesium sulfate in 300 ml of dry THF was heated to reflux under nitrogen. 4.89 g (0.036 mole) of phenylurea in 125 ml of dry THF was added over a period of 1 hour. Refluxing was continued for an additional 40 minutes before the reaction mixture was filtered and the filtrate evaporated in vacuo to yield 8.23 g of a brown oil. The crude product was purified by silica gel column chromatography on 410 g of CC-7 silica gel eluting with a 7.5% ethyl acetate/hexane solution. The eluate was evaporated in vacuo to yield 4.74 g of the title compound, a white solid, mp 128°-130° C.

Provenance & Evidence