Reaction #447174

Reaction equation

1-[(4-butylphenyl)methyl]-3-(4-chloro-2-methylphenyl)-1-[6-[(methylsulfonyl)oxy]hexyl]urea

potassium chloride

dimethyl sulfoxide

→

brown oil

Yield 86.0%

1-[(4-Butylphenyl)methyl]-1-(6-chlorohexyl)-3-(4-chloro-2-methylphenyl)urea

Yield 86.0%

Solvents

water

Conditions

Workup

1. 1
   Temperaturewas heated at an oil bath temperature of 60°-80° C. for 16 hours
2. 2
   Extractionextracted with dichloromethane
3. 3
   WashThe organic layer was washed with three 40 ml portions of brine
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   OtherThe filtrate was evaporated in vacuo

Procedure

A mixture of 2.0 g of 1-[(4-butylphenyl)methyl]-3-(4-chloro-2-methylphenyl)-1-[6-[(methylsulfonyl)oxy]hexyl]urea, 0.74 g of potassium chloride, and 3.0 ml of dimethyl sulfoxide was heated at an oil bath temperature of 60°-80° C. for 16 hours. The mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with three 40 ml portions of brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated in vacuo to yield 1.5 g of a brown oil. The oil was purified by chromatography to yield 1.5 g of the desired product as a light yellow oil in 86% yield.

Source