Phosphorus oxychloride → 2-Chloroimidazo[1,2-a]pyridine-3-sulfonyl chloride

HRID 2051126Notes

Reaction equation

HRID 2051126 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[S:11]([OH:14])(=O)=[O:12].P(Cl)(Cl)([Cl:17])=O>>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[S:11]([Cl:17])(=[O:14])=[O:12]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 144224132-Chloroimidazo[1,2-a]pyridine-3-sulfonic acid

Product 1

HCID 108579162-Chloroimidazo[1,2-a]pyridine-3-sulfonyl chloride

Procedure

2-Chloroimidazo[1,2-a]pyridine-3-sulfonic acid (5.0 g) is suspended in 30 ml of phosphorus oxychloride and refluxed for 5 hours. After cooling, the reaction solution is poured into 250 ml of ice water and extracted with dichloromethane. The dichloromethane layer is collected, dried on anydrous sodium sulfate and then concentrated to dryness under reduced pressure to afford 4.6 g of the title compound as pale yellowish crystals.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane
  4. customThe dichloromethane layer is collected
  5. dry with materialdried on anydrous sodium sulfate
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b91dec64a93c49ad9f6f4b6bc3ccd85c
Source dataset
uspto-grants-1991_05
Patent number
US05017212

Reaction notes

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