Methanesulfonate → Phthalimide

HRID 1252500Notes

Reaction equation

HRID 1252500 reaction equation
S([O-])(=O)(=O)C.[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.[K].C(OC(=O)C)C.CCCCCC>CN(C=O)C>[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12

Participants

5

Reactant 3

HCID 85257MethanesulfonateHCID 21226206Ethyl acetate hexaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 6809PhthalimideYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude mesylate thus obtained was immediately taken up in 200 ml DMF, potassium phthalimide (14.44 g, (0.078 mole) was added, and the mixture was stirred at 25°-30° C. for 45 min. Completion of the reaction was judged by tracking the presence of starting material by tlc (20% ethylacetate/hexane). The reaction mixture was partitioned between water and dichloromethane, and the dichloromethane layer was dried over K2CO3 and concentrated to a brown semi-solid. This material was dissolved in ether, washed with water, decolorized again with carbon, dried over K2CO3, and filtered and concentrated. The resulting pale yellow solid was recrystallized from hexane/ethyl acetate to provide a total of 3.89 g (20%) phthalimide.

Workup

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. dry with materialthe dichloromethane layer was dried over K2CO3
  3. concentrationconcentrated to a brown semi-solid
  4. dissolutionThis material was dissolved in ether
  5. washwashed with water
  6. dry with materialdried over K2CO3
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting pale yellow solid was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-b7fd2a42f1b24824a4780361552487bf
Source dataset
uspto-grants-1988_05
Patent number
US04743617

Reaction notes

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