Reaction #6282

Reaction equation

1,2-di-propionylaminobenzene

4-bromo-1-chlorobutane

→

desired product

Yield 12.6%

1,2-bis[N-(4-chlorobutyl)-N-propionylamino]benzene

Yield 12.6%

Solvents

toluene

sodium hydroxide

Conditions

Workup

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   OtherThe organic layer was separated
3. 3
   Washwashed with saturated aqueous sodium chloride
4. 4
   Otherdried
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   Otherthe residue was purified by column chromatography (eluent: hexane/ethyl acetate =2 :1 to 1:1 to 1:2 to 1:4)

Procedure

To a suspension of 3.27 g (15 mmol) of 1,2-di-propionylaminobenzene, 4.32 ml (37.5 mmol) of 4-bromo-1-chlorobutane, and 0.96 g (3.0 mmol) of tetrabutylammonium bromide in 25 ml of toluene, 5.6 ml of 50% aqueous sodium hydroxide was added at room temperature, and the mixture was stirred for 16 hours. The organic layer was separated, washed with saturated aqueous sodium chloride, and dried. The solvent was distilled off and the residue was purified by column chromatography (eluent: hexane/ethyl acetate =2 :1 to 1:1 to 1:2 to 1:4) to give 0.76 g of the desired product (12.6% yield, white crystals).

Source