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

HRID 1444579Notes

Reaction equation

HRID 1444579 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC(OCC)OCC)C>[C:2]1([C:1]2[O:8][CH:11]=[N:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11955Benzoylhydrazine

Product 1

HCID 132171,3,4-Oxadiazole, 2-phenyl-Yield 5,695%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of the benzoic hydrazide (22.5 g, 165 mmol), triethylorthoformate (150 mL) and p-toluenesulfonic acid (300 mg) was heated at 120° C. for 12 h. Excess triethylorthoformate was removed under vacuum and the residue was purified by silica gel column chromatography to produce 2-phenyl-[1.3.4]-oxadiazole (14.5 g).

Workup

  1. customExcess triethylorthoformate was removed under vacuum
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a64e2ba73cff4ed4ab2cb61598dba44a
Source dataset
uspto-grants-2010_02
Patent number
US07662849B2

Reaction notes

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