Phosphorus oxychloride → 2-Chloro-4-phenylthiazole

Reaction equation

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

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 6989032-Hydroxy-4-phenylthiazole

Product 1

HCID 27613592-Chloro-4-phenylthiazoleYield 57%

Procedure

4-Phenyl-3H-thiazol-2-one (5 g, 28.2 mmol) was dissolved in POCl3 (30 mL), and the mixture was refluxed overnight. The mixture was concentrated in vacuum, and the residue was purified by column chromatography to give 2-chloro-4-phenylthiazole (3.1 g, 57%).

Workup

temperaturethe mixture was refluxed overnight
concentrationThe mixture was concentrated in vacuum
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-1cc5365b28cf420f811c50c15b2f1e98
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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