Phosphorus oxychloride → 2-Chloro-4-phenylthiazole

HRID 2263356Notes

Reaction equation

HRID 2263356 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]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517449HCID 178517449, compound

Product 1

HCID 27613592-Chloro-4-phenylthiazoleYield 65.2%

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

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionThe residue was poured to ice water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-41fa803d4b4941b2aba444587b98589a
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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