1,3-Dibromopropane → N-3-Bromopropylphthalimide

HRID 1886311Notes

Reaction equation

HRID 1886311 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].CC(N(C)C)=O.[Br:19][CH2:20][CH2:21][CH2:22]Br>O>[Br:19][CH2:20][CH2:21][CH2:22][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

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 31374DimethylacetamideHCID 24194345Phthalimide potassium salt

Product 1

HCID 21611N-3-BromopropylphthalimideYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

90 g of potassium phthalimide was mixed with 300 ml of dimethylacetamide and stirred. 74 ml of 1,3-dibromopropane was added to the system. The system was then allowed to undergo reaction at a temperature of 120° C. over 4 hours. The reaction solution was poured into 1 l of water. The resulting crystals were filtered off with suction. The crude crystals were recrystallized from ethanol to obtain 100 g of N-(3-bromopropyl)-phthalimide (7). (Yield: 77%; m.p. 65° C.)

Workup

  1. customreaction at a temperature of 120° C. over 4 hours
  2. filtrationThe resulting crystals were filtered off with suction
  3. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-1a1ea52dd9af44df8c96f87a0fa5f500
Source dataset
uspto-grants-1992_09
Patent number
US05151357

Reaction notes

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