Phthalimide potassium salt → Phthalimide

HRID 2080157Notes

Reaction equation

HRID 2080157 reaction equation
[K].[C:2]1(=[O:12])[NH:6][C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]12>CN(C)C=O>[C:2]1(=[O:12])[NH:6][C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]12

Participants

3

Reactant 1

HCID 24194345Phthalimide potassium salt

Product 1

HCID 6809PhthalimideYield 151.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the resulting methanesultonate ester derivative (1.09 g, 3.93 mmol) in N,N-dimethylformamide (10 mL) was added phthalimide potassium salt (757 mg, 4.09 mmol), and the solution was stirred for 2 hours under reflux. This reaction mixture was cooled to room temperature, and partitioned in ethyl acetate and water. This organic layer was separated, washed with water and brine, and then, dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and a phthalimide derivative (910 mg, 71%) was obtained.

Workup

  1. temperatureunder reflux
  2. custompartitioned in ethyl acetate
  3. customThis organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-01b3623de5d545c2a493cc22a993ddac
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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