Salicylic acid, hydrazide → ortho-(5-Methyl-1,3,4-oxadiazol-2-yl)-phenol

HRID 223355

Reaction equation

HRID 223355 reaction equation
[C:1]([NH:10][NH2:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:12](OCC)(OCC)(OCC)[CH3:13]>C(O)CC>[CH3:12][C:13]1[O:9][C:1]([C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])=[N:10][N:11]=1

Participants

4

Reactant 2

HCID 13637Salicylic acid, hydrazideHCID 66221Triethyl orthoacetate

Product 1

HCID 135979760ortho-(5-Methyl-1,3,4-oxadiazol-2-yl)-phenolYield 44.5%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

90 g (0.6 mole) of salicylic acid hydrazide and 388.8 g (2.4 moles) of triethyl orthoacetate in 500 ml of n-propanol are refluxed for 84 hours. When the mixture has cooled, the precipitate is filtered off and recrystallized from a mixture of toluene and petroleum ether. 47 g of colorless crystals (26.7% of theory) are obtained; melting point 74°-76° C.

Workup

  1. temperatureWhen the mixture has cooled
  2. filtrationthe precipitate is filtered off
  3. customrecrystallized from a mixture of toluene and petroleum ether

Sources & evidence

ORD record
ord-eab5ff6792184edcb3686bb496315b85
Source dataset
uspto-grants-1982_10
Patent number
US04353904

Linked notes

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