1,3-Dibromopropane → N-3-Bromopropylphthalimide

HRID 1085276Notes

Reaction equation

HRID 1085276 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-Dibromopropane2×HCID 24194345Phthalimide potassium salt2×

Product 1

HCID 21611N-3-BromopropylphthalimideYield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution in which 18.52 g of potassium phthalimide and 200 g of 1,3-dibromopropane were suspended in 100 ml of dimethylformamide was heated under stirring at 120° C. for 6 hours, so that potassium phthalimide and 1,3-dibromopropane were reacted. Next, insoluble matters were filtered off from the reaction mixture and the filtrate was concentrated to dryness under reduced pressure. The residue was washed with hexane and then recrystallized from ethanol-water. Crystals thus obtained were collected by filtration, washed and then dried, thereby obtaining 13.8 g of N-(3-bromopropyl)phthalimide.

Workup

  1. temperaturewas heated
  2. customwere reacted
  3. filtrationNext, insoluble matters were filtered off from the reaction mixture
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure
  5. washThe residue was washed with hexane
  6. customrecrystallized from ethanol-water
  7. customCrystals thus obtained
  8. filtrationwere collected by filtration
  9. washwashed
  10. customdried

Sources & evidence

ORD record
ord-3404d1b8c2f945f8b031ee11f9f11e52
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

Loading…