Phosphorus oxychloride → HCID 10845511, compound

HRID 1977415Notes

Reaction equation

HRID 1977415 reaction equation
O=[C:2]1[C:7]2[CH:8]=[C:9]([C:11]#[N:12])[S:10][C:6]=2[CH:5]=[CH:4][NH:3]1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:2]1[C:7]2[CH:8]=[C:9]([C:11]#[N:12])[S:10][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12875894HCID 12875894, compound

Product 1

HCID 10845511HCID 10845511, compound

Procedure

A solution of 4-oxo-4,5-dihydrothieno[3,2-c]pyridine-2-nitrile (500 mg, 2.84 mmol) prepared as in F. Eloy and A. Deryckere, Bull. Soc. Chim. Belg. 1970, 79, 301) and phosphoryl chloride (5 mL) was heated at reflux for 1 hour. The formed red solution was poured onto ice and extracted with methylene chloride (2×150 mL). The dichloromethane solution was dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography with 1:10 EtOAc/hexanes to provide the title compound.

Workup

  1. temperatureat reflux for 1 hour
  2. additionThe formed red solution was poured onto ice
  3. extractionextracted with methylene chloride (2×150 mL)
  4. dry with materialThe dichloromethane solution was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography with 1:10 EtOAc/hexanes

Sources & evidence

ORD record
ord-504480ac02a941da8e2d54e202ede2fc
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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