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

HRID 1977495Notes

Reaction equation

HRID 1977495 reaction equation
N12CCCN=C1CCCCC2.Br[CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].CN(C)C(=O)C>O>[CH:14]([N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])=[CH2:13]

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 31374DimethylacetamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Over a period of 2 hours, 672 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene were added dropwise to a solution of 1016 g of N-(2-bromoethyl)phthalimide in 2.81 of N,N-dimethylacetamide. During the addition, the temperature increased to 60° C. After the addition had ended, stirring was continued for 12 hours. The batch was poured into 9 l of water and filtered, and the filtration residue was dried at 50° C. This gave 621 g of product (=90% of theory) of melting point 79-80° C.

Workup

  1. additionDuring the addition
  2. additionAfter the addition
  3. waitwas continued for 12 hours
  4. filtrationfiltered
  5. customthe filtration residue was dried at 50° C

Sources & evidence

ORD record
ord-df36acc3a2a245d1bf8641e76c68493c
Source dataset
uspto-grants-2001_05
Patent number
US06232475B1

Reaction notes

Loading…