Benzoic Acid → HCID 22613512, compound

HRID 1414840Notes

Reaction equation

HRID 1414840 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(O)(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>ClC1C=CC=CC=1>[C:1]([NH:10][NH:11][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 1049PyridineHCID 13637Salicylic acid, hydrazideHCID 24386Thionyl Chloride

Product 1

HCID 22613512HCID 22613512, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
130 °C

Procedure

15.2 g (0.1 mol) of salicylic acid hydrazide and 12.2 g (0.1 mol) of benzoic acid are suspended in 200 ml of chlorobenzene, 3.0 g (0.038 mol) of pyridine are added and the mixture is heated to 130° C. 13.1 g (0.11 mol) of thionyl chloride are added dropwise at this temperature. The product immediately separates as a white precipitate. After stirring for 1 hour at 130° C, the mixture is cooled and filtered and the product is washed with petroleum ether. N-Salicyloyl-N'-phenyl-hydrazine of melting point 260° C is thus obtained in 62% yield.

Workup

  1. temperaturethe mixture is cooled
  2. filtrationfiltered
  3. washthe product is washed with petroleum ether

Sources & evidence

ORD record
ord-2ba0a6133f184ba7a64e6c768431ef87
Source dataset
uspto-grants-1977_01
Patent number
US04002680

Reaction notes

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