تفاعل #6282

معادلة التفاعل

1,2-di-propionylaminobenzene

4-bromo-1-chlorobutane

→

desired product

المردود 12.6%

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

المردود 12.6%

المذيبات

toluene

sodium hydroxide

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر