Benzenesulfonyl chloride → 1H-Indole, 3-acetyl-1-(phenylsulfonyl)-

HRID 248494Notes

Reaction equation

HRID 248494 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[K+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>CS(C)=O.O>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:23])=[O:22])[CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 128023-AcetylindoleHCID 14797Potassium HydroxideHCID 25517Ammonium Chloride

Product 1

HCID 8485351H-Indole, 3-acetyl-1-(phenylsulfonyl)-

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 41.39 g of 3-acetyl indole in 300 ml of dimethyl sulfoxide at 0° C. was added a solution of 18.6 g of potassium hydroxide in 20 ml of water. This mixture was stirred at 0° C. for 2 hours, then 47.6 ml of benzenesulfonyl chloride was added dropwise over 40 minutes. The mixture was stirred for an additional 30 mInutes, then poured into aqueous ammonium chloride and extracted several times with ether. The ether extracts were combined, washed with water, dried and evaporated, giving 59.8 g of 3-acetyl-N-phenylsulfonyl indole.

Workup

  1. stirringThe mixture was stirred for an additional 30 mInutes
  2. extractionextracted several times with ether
  3. washwashed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-3dcfc7d0edb84b4c8073d9f8123bacf1
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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