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

HRID 982171Notes

Reaction equation

HRID 982171 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

In 30 ml of phosphorus oxychloride is suspended 5.0 g of 2-chloroimidazo[1,2-a]pyridine-3-sulfonic acid and the suspension is refluxed for 5 hours. After cooling, the reaction mixture is poured in 250 ml of ice-water and extracted with dichloromethane. The dichloromethane layer is separated and dried over anhydrous sodium sulfate and the dichloromethane is distilled off under reduced pressure to give 4.6 g of the title compound as pale yellow crystals.

Workup

  1. temperaturethe suspension is refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane
  4. customThe dichloromethane layer is separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe dichloromethane is distilled off under reduced pressure

Sources & evidence

ORD record
ord-b50b99e516b14d7c8132c1224a6d283f
Source dataset
uspto-grants-1991_02
Patent number
US04994571

Reaction notes

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