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

HRID 1977496Notes

Reaction equation

HRID 1977496 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].O>CN(C)C(=O)C>[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 962WaterHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 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 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

Over a period of 2 hours, 2.3 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene were added dropwise to a solution of 3.5 kg of N-(2-bromoethyl)phthalimide in 9.6 l of N,N-dimethylacetamide. During the addition, the temperature increased to 50° C. After the addition had ended, stirring was continued for 17 hours. The batch was poured into 29 l of water and filtered, and the filtration residue was dried at from 30 to 40° C. This gave 1.95 kg of product (=82% of theory) of melting point 79-80° C.

Workup

  1. additionDuring the addition
  2. additionAfter the addition
  3. waitwas continued for 17 hours
  4. filtrationfiltered
  5. customthe filtration residue was dried at from 30 to 40° C

Sources & evidence

ORD record
ord-4dc3406cb13645798881eee19fa35b35
Source dataset
uspto-grants-2001_05
Patent number
US06232475B1

Reaction notes

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