Acetic Acid → HCID 18993206, compound

HRID 375640Notes

Reaction equation

HRID 375640 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](C3C=CC(SC)=CC=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OO.[C:29](O)(=O)[CH3:30]>O.C(OCC)(=O)C>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([S:7]([C:1]3[CH:6]=[CH:5][C:29]([CH3:30])=[CH:3][CH:2]=3)(=[O:9])=[O:8])=[CH:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 53746941HCID 53746941, compound

Product 1

HCID 18993206HCID 18993206, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-phenylsulfonyl-3-(4-methylthiophenyl)indole (8.89 g, 23.4 mmol) in glacial acetic acid (15 mL) was added 30% H2O2 solution (2.45 g, 72 mmol) and the resulting 2-phase mixture was heated at reflux for 30 min during which time it became a solid mass. The reaction mixture was cooled to ambient temperature and diluted with H2O and ethyl acetate and the solid was filtered off. The filtrate layers were separated and the organic phase was washed with saturated aqueous NaHCO3, H2O, and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated with ethyl acetate/ether and the resulting solid was combined with the solid obtained above and recrystallized from ethyl acetate to give 8.15 g of 1-phenylsulfonyl-3-(4-methylphenylsulfonyl)indole. mp 188.9°-189.7° C.

Workup

  1. temperaturethe resulting 2-phase mixture was heated
  2. temperatureat reflux for 30 min during which time it
  3. filtrationthe solid was filtered off
  4. customThe filtrate layers were separated
  5. washthe organic phase was washed with saturated aqueous NaHCO3, H2O, and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ethyl acetate/ether
  10. customobtained above and
  11. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cace258a05bd4ff98a06cedd3c8a747a
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Reaction notes

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