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

HRID 2452

반응식

HRID 2452 반응식
[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

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 6809PhthalimideHCID 24758Sodium hydrideHCID 196899684-Chloromethyl-N-(2-methoxyphenyl)benzamide

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0629cd8f2ed34187aae991fef93b63da
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728835

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