Benzenesulfonyl chloride → 1-Phenylsulfonylpyrrole

HRID 248487Notes

Reaction equation

HRID 248487 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C)C=O>[C:8]1([S:14]([N:3]2[CH:7]=[CH:6][CH:5]=[CH:4]2)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8027PyrroleHCID 24758Sodium hydride

Product 1

HCID 1401461-PhenylsulfonylpyrroleYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 1.056 g of prewashed sodium hydride in 50 ml of dimethylformamide at 0° C. was added dropwise a solution of 1.34 g of pyrrole in 50 ml of dimethylformamide. The mixture was stirred for 30 minutes, then a solution of 3.89 g of benzenesulfonyl chloride in dimethylformamide was added. This mixture was stirred at room temperature for 18 hours, then slowly quenched with water and extracted several times with ether. The extracts were combined, washed with water, dried and evaporated, giving 2.9 g of 1-(phenylsulfonyl)-1H-pyrrole.

Workup

  1. stirringThis mixture was stirred at room temperature for 18 hours
  2. customslowly quenched with water
  3. extractionextracted several times with ether
  4. washwashed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-d9fc3d7beabc4752bee100eaa6d8f023
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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