Phosphorus oxychloride → HCID 13567772, compound

HRID 280195Notes

Reaction equation

HRID 280195 reaction equation
[I:1][C:2]1[C:3](=O)[NH:4][CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:3]1[C:2]([I:1])=[CH:7][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13567771HCID 13567771, compound

Product 1

HCID 13567772HCID 13567772, compound

Procedure

A suspension of 9.0 g of 3-iodo-5-(methylsulfonyl)-2(1H)-pyridinone in 30 ml of phosphorus oxychloride was refluxed under nitrogen for 4 hours and gave a homogeneous mixture. This solidified on cooling and unreacted phosphorus oxychloride was removed under reduced pressure. The resulting white solid residue was dissolved in methylene chloride and extracted first with water and twice with aqueous 1N sodium hydroxide solution. The mixture was shaken until the aqueous phase remained basic. The methylene chloride solution was then dried over magnesium sulfate and concentrated to leave a white solid residue. This was recrystallized from ethyl acetate/hexane to give 2-chloro-3-iodo-5-(methylsulfonyl)pyridine as colorless needles melting at about 178.5°-180.5° C.

Workup

  1. temperaturewas refluxed under nitrogen for 4 hours
  2. customgave a homogeneous mixture
  3. temperatureon cooling
  4. customunreacted phosphorus oxychloride was removed under reduced pressure
  5. dissolutionThe resulting white solid residue was dissolved in methylene chloride
  6. extractionextracted first with water and twice with aqueous 1N sodium hydroxide solution
  7. dry with materialThe methylene chloride solution was then dried over magnesium sulfate
  8. concentrationconcentrated
  9. customto leave a white solid residue
  10. customThis was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-9e5c34b1bed642a9af47665ce8df8f21
Source dataset
uspto-grants-1986_05
Patent number
US04588733

Reaction notes

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