Water → HCID 53746941, compound

HRID 375639Notes

Reaction equation

HRID 375639 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[K+].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(COC)OC>[C:20]1([S:26]([N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([C:6]3[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=3)=[CH:10]2)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 18993308HCID 18993308, compound

Product 1

HCID 53746941HCID 53746941, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 3-(4-methylthiophenyl)indole (7.34 g, 30.7 mmol), prepared as in step 1, in dimethoxyethane (75 mL) was added powdered KOH (85%, 7.01 g, 125 mmol) and benzenesulfonyl chloride (4.25 mL, 33.3 mmol). A white precipitate formed immediately and the reaction mixture became quite warm. The reaction mixture was stirred for 1 hour during which time it cooled to ambient temperature. Water (50 mL) was added and the mixture was extracted with ethyl acetate. The organic phase was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo. 1-phenylsulfonyl-3-(4-methylthiophenyl)indole (8.89 g, 76% yield) was obtained by chromatography on silica gel (10%, then 20% ethyl acetate/hexanes).

Workup

  1. customA white precipitate formed immediately
  2. temperaturethe reaction mixture became quite warm
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0dc6f0ae5c64039ab8e88c66e5f02d6
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Reaction notes

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