1,4-Dichloro-2-butene, (2E)- → 2-((2E)-4-chlorobut-2-en-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1609463

Reaction equation

HRID 1609463 reaction equation
[Cl:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5]Cl.[K].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12>CN(C)C=O>[Cl:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5][N:12]1[C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]2[C:8]1=[O:18]

Participants

4

Reactant 2

HCID 6421971,4-Dichloro-2-butene, (2E)-HCID 24194345Phthalimide potassium salt

Product 1

HCID 57093742-((2E)-4-chlorobut-2-en-1-yl)-2,3-dihydro-1H-isoindole-1,3-dioneYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10 g of 1,4-dichloro(trans) 2-butene in 100 ml of N,N-dimethylformamide was added 16.5 g of phthalimide potassium with ice cooling. The mixture was stirred at room temperature for 8 hours, the mixture was subjected to extraction with water-ethyl acetate, and the organic layer was distilled to remove the solvent. The residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), giving 9.6 g of N-[4-chloro(trans) 2-butenyl]phthalimide (yield 51% ).

Workup

  1. extractionthe mixture was subjected to extraction with water-ethyl acetate
  2. distillationthe organic layer was distilled
  3. customto remove the solvent
  4. customThe residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-ac6ba98046564b4f8630d78dba4a7e2c
Source dataset
uspto-grants-1995_03
Patent number
US05401739

Linked notes

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