Phosphorus oxychloride → 4-Chloro-6-(4-methoxyphenyl)thieno[3,2-c]pyridine

HRID 1251186Notes

Reaction equation

HRID 1251186 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:14][C:13](=O)[C:12]3[CH:16]=[CH:17][S:18][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:13]1[C:12]2[CH:16]=[CH:17][S:18][C:11]=2[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 225033756(4-Methoxyphenyl)-5h-thieno[3,2-c]pyridin-4-one

Product 1

HCID 225029374-Chloro-6-(4-methoxyphenyl)thieno[3,2-c]pyridineYield 73%

Conditions

Temperature
120 °C

Procedure

6-(4-Methoxyphenyl)-5H-thieno[3,2-c]pyridin-4-one (9.1 g) was added to phosphorus oxychloride (90 g), and the mixture was heated at 120° C. for 3 hr. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and water. The organic layer was washed with water, an aqueous solution of saturated sodium bicarbonate and brine, and dried over magnesium sulfate. The solvent was evaporate, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a white powder (6.6 g, yield; 73%).

Workup

  1. customThe reaction solution was evaporated
  2. additionto the resulting residue were added ethyl acetate and water
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous solution of saturated sodium bicarbonate and brine, and dried over magnesium sulfate
  5. customThe solvent was evaporate
  6. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-510173e20ed347ca8a89a436ac745ea6
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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