1,2-Dibromoethane → 1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethoxy)-

HRID 1656142Notes

Reaction equation

HRID 1656142 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].[Br:13][CH2:14][CH2:15]Br.C(N(CC)CC)C>CN(C)C=O>[Br:13][CH2:14][CH2:15][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]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 8471TriethylamineHCID 10665N-Hydroxyphthalimide

Product 1

HCID 1998751H-Isoindole-1,3(2H)-dione, 2-(2-bromoethoxy)-Yield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 32.6 g of N-hydroxyphthalimide in 240 ml of dimethylformamide and introduce, into this solution, 74 g of 1,2-dibromoethane and then 40 g of triethylamine. Stir the reaction mixture at room temperature for 20 hours and then filter the crystals which have precipitated. Pour the filtrate into 1500 ml of cold water and isolate the white precipitate formed. After washing with water and drying in an oven, the product is obtained, with a 60% yield, which melts at 98° C.

Workup

  1. filtrationfilter the crystals which
  2. customhave precipitated
  3. additionPour the filtrate into 1500 ml of cold water
  4. customisolate the white precipitate
  5. customformed
  6. washAfter washing with water
  7. customdrying in an oven
  8. customthe product is obtained, with a 60% yield, which melts at 98° C.

Sources & evidence

ORD record
ord-093bd2d8788d475a9e6e7a29ff78b002
Source dataset
uspto-grants-1993_10
Patent number
US05252749

Reaction notes

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