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

HRID 1642097

Reaction equation

HRID 1642097 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-f81910309c004b8eace99061811cd35d
Source dataset
uspto-grants-2012_02
Patent number
US08119642B2

Linked notes

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