异丙醇 → N-(3-氯苯基)邻苯二甲酰亚胺

HRID 5273

反应方程式

HRID 5273 反应方程式
C(O)(C)C.[ClH:5].CNOC.Br[CH2:11][CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].C(=O)(O)[O-].[Na+]>C(N(CC)CC)C>[Cl:5][CH2:11][CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24]

参与物

6

反应物 4

HCID 3776异丙醇HCID 21611N-(3-溴丙基)苯二胺HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892碳酸氢钠

产物 1

HCID 245265N-(3-氯苯基)邻苯二甲酰亚胺收率 46.1%

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 mol of isopropanol containing N,O-dimethylhydroxylamine hydrochloride (3.97 g, 40.0 mmol) was added dropwise 5.56 ml of triethylamine. After 5 minutes, there was added 2.68 g (10.0 mmol) of N-(3-bromopropyl)phthalimide and the mixture was refluxed for 33 hours. This was cooled to room temperature, then poured into 200 ml of 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 1.03 g of N-(3-chloropropyl)phthalimide and further development with chloroform resulted in 1.21 g (yield: 53%) of white crystals of N-[3-(N-methoxy-N-methylamino)propyl]-phthalimide.

后处理

  1. temperaturethe mixture was refluxed for 33 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-a7a6cc20410049fab1aec4b794941182
来源数据集
uspto-grants-1993_09
专利号
US05244487

关联笔记

加载中…