1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → 2-(2-Diethoxyphosphorylethyl)isoindole-1,3-dione

HRID 1449196Notes

Reaction equation

HRID 1449196 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[P:15]([O:22]CC)([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]>>[C:8]1(=[O:9])[N:4]([CH2:3][CH2:2][P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[C:5](=[O:14])[C:6]2=[CH:13][CH:12]=[CH:11][CH:10]=[C:7]12

Participants

3

Reactant 2

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 31215Triethyl phosphite

Product 1

HCID 2543772-(2-Diethoxyphosphorylethyl)isoindole-1,3-dione

Procedure

A mixture of 5.32 g (0.017 mol) of N-(2-bromoethyl)phthalimide and 2.74 g (0.017 mol) of triethyl phosphite is heated gently to initiate reaction. After the reaction subsides, heating is continued for 1 hour with distillation of ethyl bromide. Chloroform is added to the cooled mixture and the solution is washed with water. The organic phase is dried and concentrated to give diethyl phthalimidoethylphosphonate.

Workup

  1. temperatureis heated gently
  2. customreaction
  3. customAfter the reaction subsides
  4. temperatureheating
  5. distillationis continued for 1 hour with distillation of ethyl bromide
  6. additionChloroform is added to the cooled mixture
  7. washthe solution is washed with water
  8. customThe organic phase is dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-26b949254c864171b21aa5d7904008be
Source dataset
uspto-grants-1980_02
Patent number
US04189573

Reaction notes

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