Diethyl Ether → 2-(2-Chlorocyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione

HRID 1074145Notes

Reaction equation

HRID 1074145 reaction equation
Cl[C:2]1[CH:7]([Cl:8])[CH2:6][CH2:5][CH2:4][CH:3]=1.[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K].[I-].[K+].C(OCC)C>CN(C)C=O>[Cl:8][C:7]1[CH:2]([N:13]2[C:9](=[O:19])[C:10]3[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:12]2=[O:14])[CH2:3][CH2:4][CH2:5][CH:6]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 4875Potassium IodideHCID 12211415HCID 12211415, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 144239792-(2-Chlorocyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dioneYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 11.0 g (72.8 mmol) 1,6-dichlorocyclohexene, 20.0 g (108 mmol) potassium phthalimide and 1.0 g (6.0 mmol) potassium iodide in 50 ml dry dimethylformamide was stirred 24 hours at 110° C. under an atmosphere of nitrogen. The reaction mixture was allowed to cool then poured into 30 ml diethyl ether. The dark mixture was filtered then ether and DMF removed in vacuo. The dark crystalline residue was dissolved in ethyl acetate then chromatographed on 500 g flash silica eluting with 10% to 20% ethyl acetate/hexane. Concentration of appropriate fractions followed by recrystallization from ethyl acetate/hexane gave 14.0 g (73.5%) of the desired phthalimide, mp 99°-103° C.

Workup

  1. temperatureto cool
  2. filtrationThe dark mixture was filtered
  3. customether and DMF removed in vacuo
  4. dissolutionThe dark crystalline residue was dissolved in ethyl acetate
  5. customthen chromatographed on 500 g flash silica eluting with 10% to 20% ethyl acetate/hexane
  6. customConcentration of appropriate fractions followed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7adae9eb705c475c82e314356ec2d4e6
Source dataset
uspto-grants-1990_11
Patent number
US04973585

Reaction notes

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