Phosphorus oxychloride → 2-Chloro-4-phenylthiazole
Reaction equation
[C:1]1([C:7]2[N:8]=[C:9](O)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:15])=O>>[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]=1Participants
3
Procedure
A mixed solution of 4-phenyl-1,3-thiazol-2-ol (2.00 g, 11.3 mmol) in phosphorus oxychloride (20 ml) was stirred at 100° C. for 2 hours. The solvent was distilled off under reduced pressure. The residue was poured to ice water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 1.44 g (65.2%) of the desired product as a solid.
Workup
- distillationThe solvent was distilled off under reduced pressure
- additionThe residue was poured to ice water
- extractionextracted with ethyl acetate