Iodine → trans-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide

HRID 6718Notes

Reaction equation

HRID 6718 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]\[CH2:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH:5]=[CH:6][CH:7]=1.II>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[CH2:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 807IodineHCID 58679826cis-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide

Product 1

HCID 10710192trans-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimideYield 26.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of cis-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide (1.9 g) and iodine (50 mg) in 500 mL toluene was irradiated for 5 days with a 100-watt incandescent light bulb. The solvent was removed in vacuo and the residue was recrystallized from toluene/methanol to give 0.50 g of trans-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide (no cis-isomer was observed by 1H-NMR).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was recrystallized from toluene/methanol

Sources & evidence

ORD record
ord-4a13bbd2a60c451086842b48e8e24bdf
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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