Ethyl Bromide → 2-Ethoxy-1H-isoindole-1,3(2H)-dione

HRID 1980238Notes

Reaction equation

HRID 1980238 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].O.O.O.[C:16]([O-])(=O)[CH3:17].[Na+].C(Br)C>CS(C)=O.C(Cl)(Cl)Cl>[CH2:16]([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])[CH3:17]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 10665N-HydroxyphthalimideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 5959292-Ethoxy-1H-isoindole-1,3(2H)-dioneYield 68.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 24 g (0.147 moles) of N-hydroxyphthalimide in 120 ml of dimethyl sulfoxide is warmed at 40° up to complete dissolution. Then 23.9 g (0.176 moles) of sodium acetate trihydrate and 15.92 ml (0.21 moles) of ethyl bromide are added, while warming at 80° C. After two hours and 15 minutes, the mixture is diluted with 600 ml of chloroform, washed with 10% potassium bicarbonate and dried. Removal of the solvent leaves 19.3 g (68.7%) of N-ethoxy-phthalimide, melting point 95°-97° C. (A. Rougny et al, Bull. Soc. Chim. Fr. 1976, pp. 833).

Workup

  1. dissolutiondissolution
  2. washwashed with 10% potassium bicarbonate
  3. customdried
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-7f46da217cce45b99a2288450f7fa704
Source dataset
uspto-grants-1985_04
Patent number
US04508719

Reaction notes

Loading…