Dichloromethane → 5-Pyridin-3-yl-thiophene-2-sulfonyl chloride

HRID 1636790

Reaktionsgleichung

Reaktionsgleichung von HRID 1636790
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[Li]CCCC.[S:17](Cl)([Cl:20])(=[O:19])=[O:18].C(Cl)Cl>C1COCC1>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:2]2[S:1][C:5]([S:17]([Cl:20])(=[O:19])=[O:18])=[CH:4][CH:3]=2)[CH:7]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 5951453-(2-Thienyl)pyridineHCID 178418339Butyllithium

Produkt 1

HCID 106589765-Pyridin-3-yl-thiophene-2-sulfonyl chlorideAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-thiophen-2-yl-pyridine (0.35 g, 2.20 mmol) in 15 mL of THF at -78° C. is added n-BuLi (1.44 mL of a 1.6M solution in hexanes, 2.31 mmol). After stirring for 15 minutes, SO2 gas is bubbled through the solution for 30 minutes. The solution is then allowed to warm to room temperature and stirred overnight. The solution is concentrated to dryness and the resulting solid is suspended in 20 mL of hexane. Sulfuryl chloride (0.185 mL, 2.31 mmol) is added and the reaction mixture is stirred for 30 minutes and then a small amount of methylene chloride is added and the mixture is stirred for another 30 minutes. The mixture is then concentrated to dryness and diluted with ethyl acetate and washed with saturated NaHCO3 (aq), water and brine. The organic layer is dried over MgSO4, filtered and concentrated to give a brown solid as the title product (0.452 g, 1.74 mmol) which is used in the subsequent step without further purification.

Aufarbeitung

  1. customSO2 gas is bubbled through the solution for 30 minutes
  2. stirringstirred overnight
  3. concentrationThe solution is concentrated to dryness
  4. stirringthe reaction mixture is stirred for 30 minutes
  5. stirringthe mixture is stirred for another 30 minutes
  6. concentrationThe mixture is then concentrated to dryness
  7. additiondiluted with ethyl acetate
  8. washwashed with saturated NaHCO3 (aq), water and brine
  9. dry with materialThe organic layer is dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-662596773ac24d7da58b54eed794752d
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06034093

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