6-Bromo-1-hexene → N-(Hex-5-enyl)phthalimide

HRID 463795

Reaction equation

HRID 463795 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].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19]>CN(C)C(=O)C>[C:1]1(=[O:11])[N:5]([CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 2

HCID 759066-Bromo-1-hexeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 12422290N-(Hex-5-enyl)phthalimideYield 100%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A suspension of 39 g of potassium phthalimide in 150 ml of N,N-dimethylacetamide was treated at 20° C. while stirring with 27 ml of 6-bromo-1-hexene. After 4 hours, the mixture was poured into 300 ml of ice-water, extracted with ether, the organic phase was washed with 10% sodium chloride solution, dried, filtered and concentrated to dryness. There were obtained 45 g (100%) of 6-phthalimido-1-hexene, m.p. 17°-20° C.

Workup

  1. additionwas treated at 20° C.
  2. extractionextracted with ether
  3. washthe organic phase was washed with 10% sodium chloride solution
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9f8808b26aa441a2b50aeb13a06dffd9
Source dataset
uspto-grants-1985_10
Patent number
US04544748

Linked notes

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