反应 #5368

反应方程式

isopropanol

N,O-dimethylhydroxylamine hydrochloride

sodium bicarbonate

N-(bromoethyl)phthalimide

→

N-(2-chloroethyl)-phthalimide

收率 65.4%

溶剂

triethylamine

反应条件

后处理

1. 1
   温度the mixture was refluxed for 29 hours
2. 2
   萃取extracted with chloroform
3. 3
   其他The organic layer was separated
4. 4
   洗涤was washed with water
5. 5
   干燥dried over magnesium sulfate
6. 6
   workup.DISTILLATIONChloroform was distilled off
7. 7
   其他the residue was purified by column chromatography on silica gel

实验过程

To a suspension of 50 ml of isopropanol containing N,O-dimethylhydroxylamine hydrochloride (3.90 g, 40.0 mmol) was added dropwise 5.56 ml of triethylamine. The resulting mixture became homogeneous after 5 minutes. Thereto was added 2.45 g (10.0 mmol) of N-(bromoethyl)phthalimide and the mixture was refluxed for 29 hours. This was cooled to room temperature, then poured into 200 ml of a saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was separated and was washed with water and dried over magnesium sulfate. Chloroform was distilled off and the residue was purified by column chromatography on silica gel. Development with 30% hexane-chloroform resulted in elution of 1.37 g of N-(2-chloroethyl)-phthalimide and further development with chloroform resulted in 0.964 g (yield: 41%) of white cyrstals of N-[2-(N-methoxy-N-methylamino)ethyl]phthalimide.

来源