1,3-Dibromopropane → N-3-Bromopropylphthalimide

HRID 1729278Notes

Reaction equation

HRID 1729278 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:13][CH2:14][CH2:15][CH2:16]Br>CN(C)C=O>[Br:13][CH2:14][CH2:15][CH2:16][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

4

Reactant 2

HCID 80011,3-DibromopropaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 21611N-3-BromopropylphthalimideYield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

18.52 g of potassium phthalimide and 200 g of 1,3-dibromopropane were suspended in 100 ml of dimethylformamide, and the suspension was then stirred at 120° C. for 6 hours under heating to react them. Next, insolubles were removed from the resultant reaction mixture by filtration, and the filtrate was then concentrated to dryness under reduced pressure. The residue was washed with hexane, and then recrystallized from ethanol/water, and the resultant crystals were collected by filtration, washed, and then dried, thereby obtaining 13.8 g of N-(3-bromopropyl)phthalimide.

Workup

  1. temperatureunder heating
  2. customto react them
  3. customNext, insolubles were removed from the resultant
  4. customreaction mixture
  5. filtrationby filtration
  6. concentrationthe filtrate was then concentrated to dryness under reduced pressure
  7. washThe residue was washed with hexane
  8. customrecrystallized from ethanol/water
  9. filtrationthe resultant crystals were collected by filtration
  10. washwashed
  11. customdried

Sources & evidence

ORD record
ord-1d36e95a2e76415b97d51bf0cb877cb3
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

Loading…