Chlorosulfonic acid → 5-Pyridin-4-yl-thiophene-2-sulfonyl chloride

HRID 2296666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2296666
[Cl:1][S:2]([OH:5])(=O)=[O:3].[N:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1.C([O-])(O)=O.[Na+]>>[N:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:15][CH:16]=2)=[CH:8][CH:7]=1

Komponenten

4

Edukt 3

HCID 24638Chlorosulfonic acidHCID 516892Sodium BicarbonateHCID 5952454-(2-Thienyl)pyridine

Produkt 1

HCID 106350455-Pyridin-4-yl-thiophene-2-sulfonyl chlorideAusbeute 32,7 %

Versuchsvorschrift

Chlorosulfonic acid (1.4 ml) was added to 2-(4-pyridyl)thiophene (500 mg) at 0° C. and the mixture was stirred for 5 days at room temperature. Ice-water was carefully added to this mixture at 0° C. to decompose excess reagent. This solution was poured into saturated aqueous NaHCO3 solution (ca. pH 7) and extracted with AcOEt (20 ml×3). The combined organic layer was washed with brine, and dried over MgSO4. After 4N HCl-AcOEt (10 ml) was added to the solution, the solvent was removed in vacuo to give 300 mg of 5-(4-pyridyl)-thiophenesulfonyl chloride as a white solid (yield 32.7%).

Aufarbeitung

  1. extractionextracted with AcOEt (20 ml×3)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. additionAfter 4N HCl-AcOEt (10 ml) was added to the solution
  5. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9cf965a09b0b4134870a5be86d9d384d
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489324B2

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