Dimethylformamide → N-propoxyphthalimide

HRID 1863504Notes

Reaction equation

HRID 1863504 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(N(CC)CC)C.Br[CH2:21][CH2:22][CH3:23].CN(C)C=O>O>[CH2:21]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])[CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78401-BromopropaneHCID 8471TriethylamineHCID 10665N-Hydroxyphthalimide

Product 1

HCID 2768912N-propoxyphthalimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 212 g. of N-hydroxyphthalimide, 132 g. of triethylamine, 160 g. of 1-bromopropane and 500 ml. of dimethylformamide is stirred overnight. The reaction mixture is poured into 4.5 liters of water and is stirred at ice temperature for 11/2 hours. The solid is removed by filtration, washed with water and dried in vacuo to give N-propoxyphthalimide, m.p. 51°-3° C.

Workup

  1. additionA mixture of 212 g
  2. customThe solid is removed by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4381f01c257c4ac8b5c39acfb8acb5ce
Source dataset
uspto-grants-1979_09
Patent number
US04169155

Reaction notes

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