((2-Bromoethyl)thio)benzene → 2-[2-(phenylthio)ethyl]-1H-isoindole-1,3(2H)-dione

HRID 620739Notes

Reaction equation

HRID 620739 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][CH2:15][S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[C:17]1([S:16][CH2:15][CH2:14][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 78553((2-Bromoethyl)thio)benzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 9344532-[2-(phenylthio)ethyl]-1H-isoindole-1,3(2H)-dioneYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Potassium phthalimide (5.43 g, 25 mmol) was added to a DMF (50 ml) solution of [(2-bromoethyl)thio]benzene (5,43 g, 25 mmol) and this stirred mixture under N2 was heated at 90° C. for 2 h. After cooling to room temperature, the reaction was filtered. The solvent was stripped from the filtrate under reduced pressure. The residue, dissolved in CH2Cl2 (100 ml), was filtered, concentrated, and flash chromotographed on a 4 inch column eluting with 1 to 6% EtOAc/toluene to produce 4.9 g of the title product.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction was filtered
  3. dissolutionThe residue, dissolved in CH2Cl2 (100 ml)
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. washeluting with 1 to 6% EtOAc/toluene

Sources & evidence

ORD record
ord-602a4eaf64cc4358b571028e60174ac2
Source dataset
uspto-grants-1989_04
Patent number
US04822775

Reaction notes

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