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

반응식

[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

참가 물질

반응물 3

HCID 24813Phosphorus oxychloride

HCID 24819Phosphorus pentachloride

HCID 203265625-(Phenylthio)-2-pyridone

생성물 1

HCID 111953972-Chloro-5-(phenylthio)pyridine

실험 절차

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.