Diethyl disulfide → HCID 21414079, compound

Participants

Reaction Conditions

Reaction Steps

Ethane sulfenyl chloride was prepared extemporaneously as in Example 9 from 68 g of diethyl disulfide and 67 g of sulfuryl chloride, cooled to -40° C. and a solution of 51.5 g of N-methyl-N'-(3-chloro-4-methylphenyl)-urea in 800 ml of pyridine were added thereto. The mixture was allowed to come to a temperature of -20° C. and was stirred for 11/2 hours at -20° C. The mixture was poured into a water-ice-hydrochloric acid mixture and was then extracted with methylene chloride. The organic phase was washed with water, dried and concentrated to dryness under reduced pressure and the residue was chromatographed over silica gel. The product was eluted with a 9-1 benzene-ethyl acetate mixture and the product was dissolved in ethyl ether. The ether solution was treated with activated carbon, filtered, and concentrated to dryness to obtain 19.5 g of N-methyl-N-ethylthio-N'-(3-chloro-4-methylphenyl)-urea melting at <50° C.

Provenance & Evidence