5-(3-Cyclohexene-1-yl)methylenehydantoin → 5-Cyclohexylmethylhydantoin

Participants

Reaction Conditions

Reaction Steps

Forty milliliters of ethyleneglycol monomethyl ether, 3.84 g of 5-(3-cyclohexene-1-yl)methylenehydantoin and 0.43 g of wet 10% palladium on carbon (moisture 50%) were placed in a reactor equipped with a mechanical stirrer and a reflux condenser, and the mixture was reduced while stirring at 50° C. under a hydrogen pressure of 3 kg/cm2. After 4 hours, the reaction mixture was heated to 90° C. and the resulting precipitate was dissolved, after which the palladium on carbon was removed by filtering the hot mixture. To the slurry obtained by concentrating the filtrate to about 20 ml was added 100 ml of water, by which were obtained white crystals which were then collected by filtration and washed with water, and then dried under reduced pressure at 60° C. overnight to obtain 3.50 g of 5-cyclohexylmethylhydantoin. The yield was 89.2%. The crude crystals were recrystallized from ethanol to obtain a pure product.

Provenance & Evidence