Water → 4-iodo-N-methylphthalimide

HRID 1672837Notes

Reaction equation

HRID 1672837 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.[C:13](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([CH3:13])[C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 212575765-Iodoisoindoline-1,3-dione

Product 1

HCID 673499344-iodo-N-methylphthalimideYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Iodophthalimide (358 mg, 1.31 mmol) obtained in Step 1 was dissolved in DMF (6.7 mL), and the mixture was stirred at room temperature for 4.5 hours after adding potassium carbonate (272 mg, 1.97 mmol) and methyl iodide (0.10 mL, 1.57 mmol). The mixture was further stirred for 45 minutes after adding potassium carbonate (544 mg, 3.94 mmol) and methyl iodide (1.0 mL, 15.7 mmol). Thereafter, water and ethyl acetate were added to the mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give 4-iodo-N-methylphthalimide (180 mg, 48%).

Workup

  1. stirringThe mixture was further stirred for 45 minutes
  2. customto separate the organic layer
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6fa4e4b3a17a43058b365656dc4f86f0
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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