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

HRID 231480Notes

Reaction equation

HRID 231480 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-e9f3ec7fa2234131a34ce172f1a57146
Source dataset
uspto-grants-1989_07
Patent number
US04847241

Reaction notes

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