Phosphorus oxychloride → 2-Chloro-4-phenylthiazole

HRID 1195795Notes

Reaction equation

HRID 1195795 reaction equation
O[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517449HCID 178517449, compound

Product 1

HCID 27613592-Chloro-4-phenylthiazole

Procedure

To 80 ml of phosphorus oxychloride were added 7.7 g (43 mmol) of 2-hydroxy-4-phenylthiazole, followed by heating at 100°-105° C. for 2 hours. The solvent was then distilled off from the reaction mixture under reduced pressure. Ice water was added to the residue, followed by extraction with ethyl ether. The ether layer was washed with water. After purification by silica gel column chromatography (solvent: hexane/ethyl acetate=5/1), the title compound was obtained as pale yellow crystals.

Workup

  1. temperatureby heating at 100°-105° C. for 2 hours
  2. distillationThe solvent was then distilled off from the reaction mixture under reduced pressure
  3. additionIce water was added to the residue
  4. extractionfollowed by extraction with ethyl ether
  5. washThe ether layer was washed with water
  6. customAfter purification by silica gel column chromatography (solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-bbd48428ddad4311a4e64414339d0545
Source dataset
uspto-grants-1992_05
Patent number
US05112841

Reaction notes

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