Reaktion #6282

Reaktionsgleichung

1,2-di-propionylaminobenzene

4-bromo-1-chlorobutane

→

desired product

Ausbeute 12.6%

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

Ausbeute 12.6%

Lösungsmittel

toluene

sodium hydroxide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle