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

HRID 1763475Notes

Reaction equation

HRID 1763475 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-ad7d94969ed5425f992cb9d367db801a
Source dataset
uspto-grants-1978_09
Patent number
US04112086

Reaction notes

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