Water → Phthalimide

HRID 579757Notes

Reaction equation

HRID 579757 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 E(1) tosylate (1.24 g, 2.95 mmol) and purified potassium phthalimide (1.1 g, 5.95 mmol, 2.0 equiv.) in dimethylsulfoxide (10.5 ml, Burdick and Jackson) were heated at 90°-100° C. for 3 hours (checked by TLC Et2O-pet ether 2:1, no tosylate remaining). After cooling to room temperature, water (13 ml) was added. Material began precipitating. The mixture was poured into ice water (~50 ml) and stirred for 30 minutes. The straw colored solid was harvested by filtration and washed with more water. The solid was dissolved in warm ethyl acetate (50 ml), washed with water (2×25 ml), dried (MgSO4), filtered and freed of solvent in vacuo. The remaining solid was recrystallized from isopropyl ether --EtOAc to give corresponding phthalimide, 830 mg (69%).

Workup

  1. temperaturewere heated at 90°-100° C. for 3 hours (
  2. customMaterial began precipitating
  3. additionThe mixture was poured into ice water (~50 ml)
  4. filtrationThe straw colored solid was harvested by filtration
  5. washwashed with more water
  6. dissolutionThe solid was dissolved in warm ethyl acetate (50 ml)
  7. washwashed with water (2×25 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customThe remaining solid was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-4c0272f958ba44619d7d8363f6834495
Source dataset
uspto-grants-1988_06
Patent number
US04749715

Reaction notes

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