1,3-Dibromopropane → N-3-Bromopropylphthalimide

HRID 1085262Notes

Reaction equation

HRID 1085262 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

In 100 ml of dimethylformamide were suspended 18.52 g of potassium phthalimide and 200 g of 1,3-dibromopropane, and then this suspension was heated with stirring at 120° C. for 6 hours so as to perform reaction. Next, insoluble matters were removed from the resulting 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 resulting crystals were collected by filtration, washed, and dried to obtain 13.8 g of N-(3-bromopropyl)phthalimide.

Workup

  1. temperaturethis suspension was heated
  2. customreaction
  3. customNext, insoluble matters were removed from the resulting reaction mixture by filtration
  4. concentrationthe filtrate was then concentrated to dryness under reduced pressure
  5. washThe residue was washed with hexane
  6. customrecrystallized from ethanol/water
  7. filtrationthe resulting crystals were collected by filtration
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-2dc016895dd24a66a38484ccc5c91573
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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