Benzenesulfonyl chloride → HCID 10107997, compound

HRID 2394395Notes

Reaction equation

HRID 2394395 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.CCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[C:14]1([S:20]([N:1]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=3[CH:3]=[CH:2]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 333703Indole-4-carboxaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 10107997HCID 10107997, compoundYield 73.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Indole-4-carbaldehyde (580 mg) was dissolved in 8 ml of dimethylformamide, then 176 mg of sodium hydride (content 60%) was added to the resulting solution with ice-cooling, followed by stirring for one hour, addition of 777 mg of benzenesulfonyl chloride and stirring for one hour. To the reaction solution, there were added 50 ml of ethyl acetate and 50 ml of a saturated sodium hydrogen carbonate aqueous solution followed by stirring for 30 minutes. After separation of phases, the aqueous phase was further extracted with 50 ml of ethyl acetate. The combined organic phase was washed with 50 ml of saturated common salt solution, dried over anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure to give a crude product. The crude product was subjected to silica gel chromatography (eluent: hexane/ethyl acetate=9/1) to give 842 mg of 1-benzenesulfonylindole-4-carbaldehyde as pale brown crystals. The yield thereof was found to be 74%.

Workup

  1. temperaturecooling
  2. stirringstirring for one hour
  3. stirringby stirring for 30 minutes
  4. customAfter separation of phases
  5. extractionthe aqueous phase was further extracted with 50 ml of ethyl acetate
  6. washThe combined organic phase was washed with 50 ml of saturated common salt solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customfollowed by evaporation of the solvent under reduced pressure
  9. customto give a crude product

Sources & evidence

ORD record
ord-b8ca3cf528c542ecb76b47653dd05edd
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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