Реакция #6282

Уравнение реакции

1,2-di-propionylaminobenzene

4-bromo-1-chlorobutane

→

desired product

Выход 12.6%

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

Выход 12.6%

Растворители

toluene

sodium hydroxide

Условия реакции

Обработка

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

Методика

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).

Источник