Potassium Iodide → Phthalimide

HRID 396145Notes

Reaction equation

HRID 396145 reaction equation
C1(C)C=CC(S(OCC[N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])(=O)=O)=CC=1.[I-].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O>[C:17]1(=[O:18])[NH:13][C:14](=[O:23])[C:15]2=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]12

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 2275882-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl 4-methylbenzene-1-sulfonateHCID 516892Sodium Bicarbonate

Product 1

HCID 6809PhthalimideYield 113.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 45 (500 mg) obtained in Example 1, N-{2-(p-toluenesulfonyloxy)ethyl}phthalimide (537 mg), potassium iodide (258 mg), and sodium hydrogen carbonate (131 mg) were stirred in dimethylformamide (8 ml) at 150° C. for 28 hours. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 260 mg of phthalimide compound.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-088108b6d45848b78e12448257a04382
Source dataset
uspto-grants-2003_08
Patent number
US06608061B2

Reaction notes

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