Dimethylformamide → Phthalimide

HRID 396352Notes

Reaction equation

HRID 396352 reaction equation
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.[K]>O>[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

4

Reactant 2

HCID 6228DimethylformamideHCID 24194345Phthalimide potassium salt

Product 1

HCID 6809PhthalimideYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a DMF (10 mL) solution of the above compound (0.060 g, 0.12 mmol) was added potassium phthalimide (0.046 g, 0.25 mmol) and the reaction was heated to 60° C. After heating for 20 hr the solution was cooled to RT and poured into water (40 mL), extracted with EtOAc (3×20 mL), and the organics were washed with water and brine. After drying over MgSO4, the organics were concentrated to an orange solid, then purified by silica gel column chromatography. The desired phthalimide was eluted from the column with 5% methanol/methylene chloride in 14% yield.

Workup

  1. temperatureAfter heating for 20 hr the solution
  2. temperaturewas cooled to RT
  3. extractionextracted with EtOAc (3×20 mL)
  4. washthe organics were washed with water and brine
  5. dry with materialAfter drying over MgSO4
  6. concentrationthe organics were concentrated to an orange solid
  7. custompurified by silica gel column chromatography
  8. washThe desired phthalimide was eluted from the column with 5% methanol/methylene chloride in 14% yield

Sources & evidence

ORD record
ord-9b135d52d5854ab6b05a4aef7c748b88
Source dataset
uspto-grants-2003_08
Patent number
US06608081B2

Reaction notes

Loading…