Hydrogen Peroxide → N-(3,4-Dichlorophenyl)-N'-[5-(hexylsulfanyl)-1,3,4-thiadiazol-2-yl]urea

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Reaction Steps

A solution of 6.0 g. (0.015 mole) of 1-(3,4-dichlorophenyl)-3-[5-(hexylthio)-1,3,4-thiadiazol-2-yl]urea (Example 18) was prepared in 30 ml. of glacial acetic acid. The mixture was heated to about 85°-90° C. and 4.08 g. (0.036 mole) of 30 percent hydrogen peroxide was added dropwise. After addition was complete, the temperature of the reaction mixture was maintained at about 85°-90° C. for an additional 1.5 hours. The reaction mixture was then cooled and poured onto ice. A precipitate formed which was filtered off and washed with water. The solid thus obtained was recrystallized from a mixture of ethyl acetate and normal hexane to yield product having a melting point of about 204°-206° C., and identified by elemental analyses and NMR spectrum as 1-(3,4-dichlorophenyl)-3-[5-(hexylsulfonyl)-1,3,4-thiadiazol-2-yl]urea.

Provenance & Evidence