Reacción #6282

Ecuación de reacción

1,2-di-propionylaminobenzene

4-bromo-1-chlorobutane

→

desired product

Rendimiento 12.6%

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

Rendimiento 12.6%

Disolventes

toluene

sodium hydroxide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente