반응 #6282

반응 방정식

1,2-di-propionylaminobenzene

4-bromo-1-chlorobutane

→

desired product

수율 12.6%

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

수율 12.6%

용매

toluene

sodium hydroxide

반응 조건

후처리

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

실험 절차

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).

출처