p-Toluenesulfonic acid → 1,3,4-Oxadiazole, 2-phenyl-

HRID 1624409Notes

Reaction equation

HRID 1624409 reaction equation
[CH3:1][O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[NH2:12][NH2:13].C(OC(OCC)OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCO>[C:4]1([C:3]2[O:2][CH:1]=[N:12][N:13]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7150Methyl BenzoateHCID 24654Hydrazine hydrate (1:1)HCID 31214Ethyl orthoformate

Product 1

HCID 132171,3,4-Oxadiazole, 2-phenyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Benzoic acid methyl ester (1.01 g, 7.34 mmol) and hydrazine monohydrate (10 mL) were dissolved in EtOH (20 mL) then heated in a sealed tube to 80° C. for 23 hours. The reaction was allowed to cool and then triethylorthoformate (25 mL) and p-toluenesulfonic acid (0.100 g, 0.526 mmol) were added, the tube was re-sealed, and the reaction was heated to 120° C. for 26 hours. The reaction mixture was then submitted to standard aqueous workup and purified on silica gel (0-70% EtOAc in hexanes) to afford the title compound.

Workup

  1. temperatureto cool
  2. customthe tube was re-sealed
  3. temperaturethe reaction was heated to 120° C. for 26 hours
  4. custompurified on silica gel (0-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-788778e437994e4aa385c4584e5e867f
Source dataset
uspto-grants-2014_07
Patent number
US08778983B2

Reaction notes

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