Phosphorus oxychloride → 4-Chlorothieno[3,2-c]pyridine

HRID 2761

Reaktionsgleichung

Reaktionsgleichung von HRID 2761
[S:1]1[C:9]2[CH:8]=[CH:7][NH:6][C:5](=O)[C:4]=2[CH:3]=[CH:2]1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:5]1[C:4]2[CH:3]=[CH:2][S:1][C:9]=2[CH:8]=[CH:7][N:6]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 2885254H,5H-thieno(3,2-c)pyridin-4-one

Produkt 1

HCID 128273124-Chlorothieno[3,2-c]pyridine

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5H-Thieno[3,2-c]pyridin-4-one (1.0 g, 6.62 mmol) is dissolved in 30 mL of phosphorous oxy chloride. The solution is heated to 100° C. After 4 h, the solution is concentrated. The residue is dissolved in CH2 Cl2. The resulting solution is washed with water and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 40% CH2Cl2 /hexanes to 60% CH2Cl2 /hexanes. The title compound (1.0 g, 5.8 mmol) is obtained as a white solid.

Aufarbeitung

  1. concentrationthe solution is concentrated
  2. dissolutionThe residue is dissolved in CH2 Cl2
  3. washThe resulting solution is washed with water and saturated NaCl
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by column chromatography
  8. washeluting with a gradient of 40% CH2Cl2 /hexanes to 60% CH2Cl2 /hexanes

Quellen und Nachweise

ORD-Eintrag
ord-91ec8de0a1e542cc9e6a284639bbfc6c
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731315

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