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

HRID 1636779

Reaction equation

HRID 1636779 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
100 °C

Procedure

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 hours, the solution is concentrated. The residue is dissolved in CH2Cl2. 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.

Workup

  1. concentrationthe solution is concentrated
  2. dissolutionThe residue is dissolved in CH2Cl2
  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

Sources & evidence

ORD record
ord-0c279f7fd02d414880916db47fdc6e15
Source dataset
uspto-grants-2000_03
Patent number
US06034093

Linked notes

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