Hydrochloric Acid → HCID 21414093, compound

Participants

Reaction Conditions

Reaction Steps

Ethane sulfenyl chloride was prepared as in Example 9 from 68 g of diethyldisulfide and 67 g of sulfuryl chloride, cooled to -40° C. and a solution of 60 g of N-methyl-N'-(4-bromophenyl)-urea in 800 ml of pyridine was added thereto. After stirring the reaction mixture for 30 minutes at -40° C., the temperature was allowed to rise to -20° C. and the mixture was stirred for 11/2 hours at this temperature. The mixture was poured into a mixture of water, ice and hydrochloric acid and was extracted with methylene chloride. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with a 7-3 benzene-ethyl acetate mixture. The product was dissolved in ethyl ether and the solution was treated with activated carbon, filtered and concentrated to dryness under reduced pressure. The residue was added to petroleum ether (b.p. = 65°-75° C.) and the precipitate formed was recovered by vacuum filtration to obtain 33 g of N-methyl-N-ethylthio-N'-(4-bromophenyl)-urea melting at <50° C.

Provenance & Evidence