碘化钠 → 4-[(1,3-dioxoisoindol-2-yl)methyl]-N-(2-methoxyphenyl)benzamide

HRID 2452

反应方程式

HRID 2452 反应方程式
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[H-].[Na+].Cl[CH2:15][C:16]1[CH:32]=[CH:31][C:19]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])=[O:21])=[CH:18][CH:17]=1.[I-].[Na+]>C1COCC1.CN(C=O)C>[CH3:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[NH:22][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])=[CH:32][CH:31]=1

参与物

7

反应物 4

HCID 5238碘化钠HCID 6809邻苯二甲酰亚胺HCID 24758氢化钠HCID 196899684-Chloromethyl-N-(2-methoxyphenyl)benzamide

产物 1

HCID 29945204-[(1,3-dioxoisoindol-2-yl)methyl]-N-(2-methoxyphenyl)benzamide收率 77.6%

试剂、催化剂与溶剂 2

HCID 6228N,N-二甲基甲酰胺溶剂HCID 8028四氢呋喃溶剂

实验过程

In an atmosphere of argon, phthalimide (150 mg, 1.0 mmol) was dissolved in THF (10 ml) to which was subsequently added sodium hydride (44 mg, 60%, 1.1 mmol) at room temperature. After 40 minutes of stirring at the same temperature, to this was added a DMF solution (5 ml) containing 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) and a catalytically effective amount of sodium iodide. After 2 hours of stirring at 80° C. and subsequent removal of the solvent by evaporation, the resulting residue was mixed with water (10 ml) and extracted with an ethyl acetate-methylene chloride (1:2) mixture solution. The resulting organic layer was washed with water and saturated brine and dried on anhydrous magnesium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was subjected to a silica gel column chromatography (methylene chloride-ether:hexane=2:1) and then washed with ether to obtain 300 mg (77.6%) of the title compound in the form of colorless solid.

后处理

  1. customat room temperature
  2. stirringAfter 2 hours of stirring at 80° C.
  3. customsubsequent removal of the solvent
  4. customby evaporation
  5. additionthe resulting residue was mixed with water (10 ml)
  6. extractionextracted with an ethyl acetate-methylene chloride (1:2) mixture solution
  7. washThe resulting organic layer was washed with water and saturated brine
  8. dry with materialdried on anhydrous magnesium sulfate
  9. customThereafter, the solvent was removed by evaporation
  10. washwashed with ether

来源与证据

ORD记录
ord-0629cd8f2ed34187aae991fef93b63da
来源数据集
uspto-grants-1998_03
专利号
US05728835

关联笔记

加载中…