Salicylic acid, hydrazide → Fenadiazole

HRID 223354

Reaction equation

HRID 223354 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].[CH2:12](OC(O)O)C>>[O:9]1[CH:12]=[N:11][N:10]=[C:1]1[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

Participants

3

Reactant 2

HCID 13637Salicylic acid, hydrazideHCID 5231668Orthoameisensaureathylester

Product 1

HCID 13883FenadiazoleYield 64.7%

Procedure

90 g (0.6 mole) of salicylic acid hydrazide and 355.2 g (2.4 moles) of orthoformic acid ethyl ester are refluxed for 22 hours. Excess of the ester is distilled off and the solid residue is recrystallized from ethanol. 62.9 g of colorless crystals (64.7% of theory) are obtained; melting point 112°-113° C.

Workup

  1. distillationExcess of the ester is distilled off
  2. customthe solid residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-11f395897a36407c812ff3a5df684d20
Source dataset
uspto-grants-1982_10
Patent number
US04353904

Linked notes

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