Water → Phthalimide

HRID 542220Notes

Reaction equation

HRID 542220 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 6809PhthalimideYield 124.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title B tosylate (8.11 g, 19.2 mmol) and purified potassium phthalimide (6.4 g, 34.6 mmol, 1.8 equiv.) in dimethylsulfoxide (70 ml, Burdick & Jackson) were 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) was added. Material began precipitating. The mixture was poured into ice water (~350 ml) and stirred 30 minutes. The straw colored solid was harvested by filtration and washed with more water. The solid was 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 (7.88 g) was recrystallized from isopropyl ether (~150 ml) to give corresponding phthalimide (6.35 g, 83%) TLC. Et2O-hexane 2:1, UV+vanillin Rf =0.38, trace 0.09.

Workup

  1. temperaturewere heated at 90°-100° C. for 21/2 hours (
  2. customMaterial began precipitating
  3. additionThe mixture was poured into ice water (~350 ml)
  4. filtrationThe straw colored solid was harvested by filtration
  5. washwashed with more water
  6. dissolutionThe solid was dissolved in warm ethyl acetate (150 ml)
  7. washwashed with water (3×50 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customThe remaining solid (7.88 g) was recrystallized from isopropyl ether (~150 ml)

Sources & evidence

ORD record
ord-c58d1bda160f4f6e83ec6e5cb4360011
Source dataset
uspto-grants-1987_04
Patent number
US04656185

Reaction notes

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