Water → 2-(4-Chloro-2-butenyl)-1,3-isoindolinedione

HRID 1821067

Reaction equation

HRID 1821067 reaction equation
[Cl:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5]Cl.[C:7]([NH2:18])(=[O:17])[C:8]1[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:10](N)=[O:11].[K].O>CN(C=O)C>[Cl:1][CH2:2][CH:3]=[CH:4][CH2:5][N:18]1[C:7](=[O:17])[C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10]1=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 6421971,4-Dichloro-2-butene, (2E)-HCID 53445390Potassium phthalamide

Product 1

HCID 27342002-(4-Chloro-2-butenyl)-1,3-isoindolinedioneYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Trans-1,4-dichloro-2-butene (1.14 ml, 10.8 mmol) was dissolved in DMF (27 ml) and purged with argon. Potassium pthalamide (1.00 g, 5.40 mmol) was added to the solution and the reaction was allowed to stir at room temperature overnight. The reaction was then poured into water (75 ml), which precipitated a white solid. This solid was collected by filtration and purified using silica gel chromatography (3:1 Hex: EtOAc) to afford a 76% yield (961 mg) of a white solid.

Workup

  1. custompurged with argon
  2. customprecipitated a white solid
  3. filtrationThis solid was collected by filtration
  4. custompurified

Sources & evidence

ORD record
ord-aafb5e2cd545420eacfb9a840ad315e0
Source dataset
uspto-grants-2009_10
Patent number
US07605259B2

Linked notes

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