Water → N-cinnamyloxyphthalimide

HRID 344574Notes

Reaction equation

HRID 344574 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C>[CH2:19]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 98116Bromomethylstyrene

Product 1

HCID 54477613N-cinnamyloxyphthalimideYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In 200 ml of DMF, 41.4 g of N-hydroxyphthalimide and 18 g of potassium carbonate were suspended. Fifty grams of cinnamyl bromide were added, followed by stirring at 120° C. for 5 hours. After completion of the reaction, the reaction mixture was cooled and then poured into about 500 ml of water. Crystals thus precipitated were collected by filtration, dried and then recrystallized from a mixed solvent of acetone and isopropyl ether, thereby obtaining 41.9 g of N-cinnamyloxyphthalimide. Yield: 59.1%

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled
  3. customCrystals thus precipitated
  4. filtrationwere collected by filtration
  5. customdried
  6. customrecrystallized from a mixed solvent of acetone and isopropyl ether

Sources & evidence

ORD record
ord-3862c10d92414e488b3193d8fa2922f6
Source dataset
uspto-grants-1991_10
Patent number
US05053070

Reaction notes

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