Allyl chloride → 1,3-Diallyl-5,5-dimethylhydantoin

Participants

Reaction Steps

To a slurry of 4.8 grams (0.1 mole) of a 50% sodium hydride mineral oil dispersion in 35 ml. of DMF was added portionwise with stirring 17.6 grams (0.105 mole) of 3-allyl-5,5-dimethylhydantoin. Hydrogen was evolved in this exothermic reaction. The reaction mixture was heated and stirred at 55°-60° C for 1 hour till the gas evolution ceased and a clear solution resulted. To the solution was added dropwise with stirring over a 10-minute period keeping the temperature below 80° C 9.3 grams (0.12 mole) of allyl chloride. The reaction mixture was then heated at 55°-60° C for 1.5 hours. Following cooling to room temperature, the reaction mixture was poured into 100 ml of water. An oily product was formed which was extracted using benzene and purified by vacuum distillation. The above named product was obtained in a yield of 14.15 grams (68%) boiling at 89°-92° C/0.1 mm. (Compound 3).

Provenance & Evidence