Water → Phthalimide

HRID 569841Notes

Reaction equation

HRID 569841 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K].O>CS(C)=O>[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12

Participants

5

Reactant 3

HCID 962WaterHCID 85570p-Toluenesulfonate2×HCID 24194345Phthalimide potassium salt

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title B tosylate (19.2 mmol) and purified potassium phthalimide (6.4 g, 34.6 mmol, 1.8 equiv.) in dimethylsulfoxide (70 ml, Burdick & Jackson) are heated at 90°-100° C. for 21/2 hours (checked by TLC Et2O-pet ether 2:1, no tosylate remaining). After cooling to room temperature, water (90 ml) is added. The mixture is poured into ice water (~350 ml) and stirred 30 minutes. A solid is harvested by filtration and washed with more water. The solid is dissolved in warm ethyl acetate (150 ml), washed with water (3×50 ml), dried (MgSO4), filtered and freed of solvent in vacuo. The remaining solid is recrystallized from isopropyl ether (~150 ml) to give corresponding phthalimide.

Workup

  1. temperatureare heated at 90°-100° C. for 21/2 hours (
  2. filtrationA solid is harvested by filtration
  3. washwashed with more water
  4. dissolutionThe solid is dissolved in warm ethyl acetate (150 ml)
  5. washwashed with water (3×50 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe remaining solid is recrystallized from isopropyl ether (~150 ml)

Sources & evidence

ORD record
ord-847ab8d308e6417fbdd9898e90cc30a5
Source dataset
uspto-grants-1988_03
Patent number
US04734426

Reaction notes

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