Benzenesulfonyl chloride → 1-Phenylsulfonylpyrrole

HRID 924971Notes

Reaction equation

HRID 924971 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCOC(C)=O>CN(C=O)C>[C:8]1([S:14]([N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8027PyrroleHCID 8857Ethyl AcetateHCID 24758Sodium hydride

Product 1

HCID 1401461-Phenylsulfonylpyrrole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-pyrrole (5 g, 74.5 mmol) in DMF (50 mL) was added NaH (4.5 g, 110 mmol) portionwise at 0° C., and the mixture was stirred at this temperature for 1 hour. Benzenesulfonyl chloride (19.4 g, 110 mmol) was added, and the mixture was stirred at room temperature overnight, followed by a standard aqueous/EtOAc workup and purified by column chromatography (PE:EtOAc=100:1).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. custompurified by column chromatography (PE:EtOAc=100:1)

Sources & evidence

ORD record
ord-55aa94830f4244c1a5f43219ee5cbee3
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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