Water → N-(2,3-Epoxypropyl)phthalimide

HRID 1814421Notes

Reaction equation

HRID 1814421 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.[K].[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.O>CN(C=O)C>[O:17]1[CH2:16][CH:15]1[CH2:13][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 18430EpibromohydrinHCID 24194345Phthalimide potassium salt

Product 1

HCID 21601N-(2,3-Epoxypropyl)phthalimideYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Step1: To a suspension of potassium phthalimide (5.0 g, 27 mmol) in DMF (75 ml) was added epibromohydrin (2.5 ml, 29 mmol), and the mixture was stirred at 120° C. for 3 h. After adding water, the mixture was extracted with (hexane/ethyl acetate=3/1), washed with brine, dried over magnesium sulfate, and then filtered. Concentrating under vacuum gave N-(2,3-epoxypropyl)phthalimide (2.81 g, 51%) which was used in the next step without further purification.

Workup

  1. extractionthe mixture was extracted with (hexane/ethyl acetate=3/1)
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationConcentrating under vacuum

Sources & evidence

ORD record
ord-9d8a2b0958a2451091c45b74b55117a7
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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