Perchloric Acid → Methyl phenyl-1,3,4-oxadiazole

HRID 1723037Notes

Reaction equation

HRID 1723037 reaction equation
Cl(O)(=O)(=O)=O.[C:6]([NH:9][NH:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)[CH3:7]>C(OC(=O)C)(=O)C>[CH3:7][C:6]1[O:18][C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:10][N:9]=1

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 256983Benzoic acid, 2-acetylhydrazide

Product 1

HCID 138101Methyl phenyl-1,3,4-oxadiazoleYield 32.3%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

60% Perchloric acid (12 ml) was added to a stirred suspension of 1-acetyl-2-benzoyl hydrazine (31 g, 0.174 mole) in acetic anhydride (150 ml) over 45 minutes at 5°±5° C. The solution was brought to ambient temperature over 1 hour, then filtered. The precipitate was dissolved in water (200 ml), solid sodium carbonate added to pH 9 and the product extracted with ethyl acetate. The extract was washed with water, dried over MgSO4 and concentrated to an oil. Chromatography gave 2-methyl-5-phenyl-1,3,4-oxadiazole as a gum (9 g, 30%). This was reacted with ethanolamine following the procedure of Preparation (a) above to give the title compound as an oil (5 g).

Workup

  1. filtrationfiltered
  2. dissolutionThe precipitate was dissolved in water (200 ml)
  3. additionsolid sodium carbonate added to pH 9
  4. extractionthe product extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-195099c2eeaf498e9aebcb1597e29488
Source dataset
uspto-grants-1989_08
Patent number
US04859686

Reaction notes

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