1,3-Dibromopropane → N-3-Bromopropylphthalimide

HRID 1085267Notes

Reaction equation

HRID 1085267 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

A suspension of 18.52 g of potassium phthalimide and 200 g of 1,3-dibromopropane in 100 ml of dimethylformamide was heated under stirring at 120° C. for 6 hours to react them. Insoluble matters were then filtered off from the reaction mixture and the filtrate was then concentrated to dryness under reduced pressure. The residue was washed with hexane and then recrystallized from ethanol-water. Resulting crystals were collected by filtration, washed and then dried to obtain 13.8 g of N-(3-bromopropyl)phthalimide.

Workup

  1. temperaturewas heated
  2. customto react them
  3. filtrationInsoluble matters were then filtered off from the reaction mixture
  4. concentrationthe filtrate was then concentrated to dryness under reduced pressure
  5. washThe residue was washed with hexane
  6. customrecrystallized from ethanol-water
  7. customResulting crystals
  8. filtrationwere collected by filtration
  9. washwashed
  10. customdried

Sources & evidence

ORD record
ord-75d7841ec9de4314a0ac739d94077d37
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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