[C:1]1([N:7]2[CH:13]([CH3:14])[C:11](=[O:12])[NH:10][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:15][C:16]([Cl:20])([Cl:19])[S:17]Cl.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[C:1]1([N:7]2[CH:13]([CH3:14])[C:11](=[O:12])[N:10]([S:17][C:16]([Cl:20])([Cl:19])[Cl:15])[C:8]2=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1A 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.
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