Trichloromethanesulfenyl chloride → HCID 13711663, compound

Participants

Reaction Steps

A stirred mixture of 8.0 g (0.042 mole) 1-phenyl-5-methylhydantoin, 8.6 g (0.046 mole) trichloromethylsulfenyl chloride and 1.0 g Aliquat® 336 in 100 ml methylene chloride was cooled in an ice bath. To that mixture a pre-cooled sodium hydroxide solution (4.2 g of 50% sodium hydroxide diluted to 20 g with water) was added at once. The temperature of the reaction mixture rose from 3° C. to 5° C.; stirring was continued for 10 minutes. The methylene chloride layer was separated and washed well with water, dried over magnesium sulfate and stripped to give 15.5 g of an oil. After being washed with cold hexane, the oil slowly solidified. The solid was crystallized from hexane-toluene to give 9.9 g of the above-identified product as a white solid, melting point 113°-114° C.

Provenance & Evidence