Phosphorus oxychloride → 2-Chloro-5-(phenylthio)pyridine

HRID 372734

Reaction equation

HRID 372734 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[CH:10][C:11](=O)[NH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:17])=O.P(Cl)(Cl)(Cl)(Cl)Cl>>[Cl:17][C:11]1[CH:10]=[CH:9][C:8]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 203265625-(Phenylthio)-2-pyridone

Product 1

HCID 111953972-Chloro-5-(phenylthio)pyridine

Procedure

A suspension of 5-(phenylthio)-2-pyridone (4.06 g., .02 mole) in 50 ml. of phosphorous oxychloride containing 10 g. of phosphorous pentachloride is heated at reflux for 6 hours. Excess phosphorous oxychloride is removed in vacuo and the residue is poured onto icewater mixture. The mixture is cooled and the pH adjusted to neutral with dilute aqueous sodium hydroxide. The resultant suspension is extracted with methylene chloride. The combined extracts are washed with water, dried and evaporated in vacuo to yield 2-chloro-5-(phenylthio)pyridine.

Workup

  1. temperatureat reflux for 6 hours
  2. customExcess phosphorous oxychloride is removed in vacuo
  3. additionthe residue is poured onto icewater mixture
  4. temperatureThe mixture is cooled
  5. extractionThe resultant suspension is extracted with methylene chloride
  6. washThe combined extracts are washed with water
  7. customdried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-423277c83c734a099258532c889e5f3e
Source dataset
uspto-grants-1978_05
Patent number
US04092321

Linked notes

Loading…