Salicylic Acid → HCID 22613512, compound

HRID 1414839Notes

Reaction equation

HRID 1414839 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(O)(=O)[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)O.N1C=CC=CC=1.S(Cl)(Cl)=[O:28]>ClC1C=CC=CC=1>[C:1]([NH:9][NH:10][C:12]1[CH:13]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:8])[C:2]1[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:28]

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 1049PyridineHCID 11955BenzoylhydrazineHCID 24386Thionyl Chloride

Product 1

HCID 22613512HCID 22613512, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

13.6 g (0.1 mol) of benzhydrazide and 13.8 g (0.1 mol) of salicylic acid are initially introduced into 200 ml of chlorobenzene and the mixture is heated to the boil. After adding 3.0 g (0.038 mol) of pyridine, 13.1 g (0.11 mol) of thionyl chloride are added dropwise over the course of 1 hour. The reaction starts immediately whilst the product separates out as a white precipitate. After cooling, the mixture is filtered and the product is washed with methanol and dried. N-Salicyloyl-N'-phenyl-hydrazine of melting point 259° C is thus obtained in 67% yield.

Workup

  1. temperaturethe mixture is heated to the boil
  2. additionare added dropwise over the course of 1 hour
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtered
  5. washthe product is washed with methanol
  6. customdried

Sources & evidence

ORD record
ord-728115499bfc4490906a9de7792bcc91
Source dataset
uspto-grants-1977_01
Patent number
US04002680

Reaction notes

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