异丙醇 → N-(2-氯乙基)邻苯二甲酰亚胺

HRID 5272

反应方程式

HRID 5272 反应方程式
C(O)(C)C.[ClH:5].CNOC.Br[CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C>[Cl:5][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23]

参与物

6

反应物 4

HCID 3776异丙醇HCID 11325N-(2-溴乙基)邻苯二甲酰亚胺HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892碳酸氢钠

产物 1

HCID 234274N-(2-氯乙基)邻苯二甲酰亚胺收率 65.4%

试剂、催化剂与溶剂 1

HCID 8471三乙胺溶剂

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.

后处理

  1. temperaturethe mixture was refluxed for 29 hours
  2. extractionextracted with chloroform
  3. customThe organic layer was separated
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationChloroform was distilled off
  7. customthe residue was purified by column chromatography on silica gel

来源与证据

ORD记录
ord-e26bcea9d9b94655bfa1a6ada380e790
来源数据集
uspto-grants-1993_09
专利号
US05244487

关联笔记

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