Pyridine → 5-Chloro-3-phenyl-1,2,4-oxadiazole

HRID 1195798Notes

Reaction equation

HRID 1195798 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]1([C:12]2[N:16]=[C:15](O)[O:14][N:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N1C=CC=CC=1>>[C:6]1([C:12]2[N:16]=[C:15]([Cl:3])[O:14][N:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 178517464HCID 178517464, compound

Product 1

HCID 127284435-Chloro-3-phenyl-1,2,4-oxadiazole

Procedure

To 53 g of phosphorus oxychloride were added 12.6 g (18 mmol) of 3-phenyl-1,2,4-oxadiazol-5-ol, followed by the further addition of 2.8 g (35 mmol of pyridine. The resultant mixture was heated under stirring for 8 hours. The reaction mixture was allowed to cool down to room temperature and then transferred into 500 ml of ice water. The resultant liquid mixture was extracted with ether. The extract was washed successively with water, a 5% aqueous solution of sodium hydroxide and water. The organic layer was dried and the solvent was distilled off. When the residue was left over under cooling, the title compound was obtained as pale brown crystals.

Workup

  1. extractionThe resultant liquid mixture was extracted with ether
  2. washThe extract was washed successively with water
  3. customThe organic layer was dried
  4. distillationthe solvent was distilled off
  5. waitWhen the residue was left over
  6. temperatureunder cooling

Sources & evidence

ORD record
ord-4370dca4fe0d4759bff0dd6d450dc528
Source dataset
uspto-grants-1992_05
Patent number
US05112841

Reaction notes

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