Benzenesulfonyl chloride → 1-Phenylsulfonylpyrrole

HRID 11236

Reaktionsgleichung

Reaktionsgleichung von HRID 11236
[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=O)C>[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

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 8027PyrroleHCID 24758Sodium hydride

Produkt 1

HCID 1401461-PhenylsulfonylpyrroleAusbeute 736,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of sodium hydride (60% in mineral oil, 2.4 g, 60 mmol) in DMF (100 ml) was added dropwise at an ice bath temperature a solution of pyrrole (3.35 g, 50 mmol) in DMF (5 ml). The mixture was stirred for 30 minutes at room temperature and cooled again. To the mixture was added dropwise a soluton of benzenesulfonylchloride (9.7 g, 5.5 mmol) in DMF (3 ml). The mixture was stirred for 30 minutes at room temperature and poured into ice-water, and extracted with ethylacetate. The extract was washed with water and dried. The solvent was evaporated. The obtained crystal was washed with hexane to give 1-benzenesulfonylpyrrole (8.4 g). Yield: 81%.

Aufarbeitung

  1. temperaturecooled again
  2. stirringThe mixture was stirred for 30 minutes at room temperature
  3. extractionextracted with ethylacetate
  4. washThe extract was washed with water
  5. customdried
  6. customThe solvent was evaporated
  7. washThe obtained crystal was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a974fa5d025a477aaee1506f61791129
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098201B2

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