Phosphorus oxychloride → HCID 22258262, compound

HRID 1610841Notes

Reaction equation

HRID 1610841 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12](=O)[N:11]2[CH:16]=[CH:17][NH:18][C:10]=12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:21][C:12]1[N:11]2[CH:16]=[CH:17][N:18]=[C:10]2[C:9]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 9964732HCID 9964732, compound

Product 1

HCID 22258262HCID 22258262, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.0 g (4.20 mmol) of 8-Benzoylimidazo[1,2-a]pyridin-5(1H)-one (example L, step 2) and 20.0 g (130.44 mmol) of phosphoric trichloride are dissolved in 20 ml toluene and refluxed for 1 h. The solvent is evaporated under vacuum; the crude is dissolved in 200 ml ethyl acetate and extracted with 100 ml saturated sodium hydrogen carbonate solution and 100 ml water. The organic phase is dried over magnesium sulfate, filtrated and concentrated. Petrolether is added to the residue and the precipitate is filtrated to yield 943 mg (87.5% of th.) (5-Chloroimidazo[1,2-a]-pyridin-8-yl)(phenyl)methanone.

Workup

  1. temperaturerefluxed for 1 h
  2. customThe solvent is evaporated under vacuum
  3. dissolutionthe crude is dissolved in 200 ml ethyl acetate
  4. extractionextracted with 100 ml saturated sodium hydrogen carbonate solution and 100 ml water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. additionPetrolether is added to the residue
  9. filtrationthe precipitate is filtrated

Sources & evidence

ORD record
ord-d0dd206055754426b2099b61da38459b
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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