Water → Phthalimide

HRID 569922Notes

Reaction equation

HRID 569922 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. The 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 to give corresponding phthalimide.

Workup

  1. temperatureare heated at 90°-100° C. for 21/2 hours (
  2. filtrationThe 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

Sources & evidence

ORD record
ord-26f7fcbd097e47cf9b5048c78d1e234a
Source dataset
uspto-grants-1988_03
Patent number
US04734424

Reaction notes

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