Phthalimide → HCID 53485842, compound

HRID 2221423Notes

Reaction equation

HRID 2221423 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH2:12]([C@@H:14]1[O:16][CH2:15]1)Cl.CC(C)([O-])C.[K+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(O)(C)C>[CH2:12]([C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:4]([NH:5][C:1](=[O:11])[C:2]=12)=[O:6])[C@H:14]1[O:16][CH2:15]1

Participants

6

Reactant 3

HCID 6809PhthalimideHCID 2734062(-)-EpichlorohydrinHCID 23665647Potassium tert-butoxide

Product 1

HCID 53485842HCID 53485842, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 3776IsopropanolSolvent2×

Conditions

Temperature
40 °C

Procedure

To a reaction vessel were added phthalimide 4.00 g (27.2 mmol), (R)-epichlorohydrin 4.52 g (49.0 mmol), benzyl trimethylammonium chloride 126 mg (0.68 mmol) and isopropanol 25 mL, and the mixture was stirred at 40° C. for 24 hours. To this mixture were dropped a mixture of potassium tert-butoxide 3.66 g (32.6 mmol) and isopropanol 15 mL and the mixture was stirred at 20° C. for 3 hours. After evaporation of the solvent, the condensed residue was dissolved in ethyl acetate and washed with water. The organic layer was taken and recrystallized to give (R)-glycidylphthalimide 4.90 g (Yield 89%, chemical purity 96%) as a white crystal.

Workup

  1. additionTo this mixture were dropped
  2. stirringthe mixture was stirred at 20° C. for 3 hours
  3. customAfter evaporation of the solvent
  4. dissolutionthe condensed residue was dissolved in ethyl acetate
  5. washwashed with water
  6. customrecrystallized

Sources & evidence

ORD record
ord-11e5f861fb624841989d84dfa4ac0635
Source dataset
uspto-grants-2008_05
Patent number
US07368608B2

Reaction notes

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