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

HRID 2452
Notes
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Reaction equation

HRID 2452 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0629cd8f2ed34187aae991fef93b63da
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728835

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes