Benzoic acid, p-nitro-, acetylhydrazide → 2-Methyl-5-(4-nitrophenyl)-1,3,4-oxadiazole

HRID 1665622Notes

Reaction equation

HRID 1665622 reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)(=O)[CH3:2]>O=P(Cl)(Cl)Cl>[CH3:2][C:1]1[O:16][C:6]([C:7]2[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)=[N:5][N:4]=1

Participants

3

Reactant 1

HCID 3332418Benzoic acid, p-nitro-, acetylhydrazide

Product 1

HCID 5404162-Methyl-5-(4-nitrophenyl)-1,3,4-oxadiazoleYield 89%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 4-nitro-benzoic acid N′-acetyl-hydrazide (200 mg, 8.9 mmol) in distilled POCl3 (4 mL) was refluxed at 110° C. under nitrogen for 6 hours. The reaction mixture was concentrated and the residue was quenched with 10% NaOH solution. The resulting precipitate was collected by filtration to afford 160 mg (89%) of 2-Methyl-5-(4-nitro-phenyl)-[1,3,4]oxadiazole. 1H NMR: (CDCl3): δ 8.38 (d, 2H), 8.24 (d, 2H), 2.7 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was quenched with 10% NaOH solution
  3. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-fa2e928ea702448db338410c903e51be
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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