Hydrochloric Acid → 2-Chloro-5-(5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid

HRID 1767579Notes

Reaction equation

HRID 1767579 reaction equation
[CH:1]([NH:3][NH:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]([C:14]([O:16]C)=[O:15])[CH:11]=[CH:10][C:9]=1Cl)=[O:6])=O.[ClH:19]>[OH-].[K+].CO>[Cl:19][C:11]1[CH:10]=[CH:9][C:8]([N:7]2[C:5](=[O:6])[NH:4][N:3]=[CH:1]2)=[CH:13][C:12]=1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 210939021-Formyl-4-(2-chloro-5-carbomethoxyphenyl)semicarbazide

Product 1

HCID 210939062-Chloro-5-(5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 1-formyl-4-(2-chloro-5-carbomethoxyphenyl)semicarbazide (0.03 g, 0.11 mmol) in 1.0 M KOH in methanol (MeOH) (0.44 mL) was heated at 80° C. for 72 hours and cooled to room temperature. 1.0 N HCl (0.8 mL) was added and the mixture evaporated to dryness in vacuo. The residue was taken up in MeOH (1.5 mL) and filtered. The filtrate was concentrated in vacuo to yield 0.028 g (100%) of the title intermediate as an amorphous solid. Mass Spectrum (M−H): 3:1 ratio of 238 and 240.

Workup

  1. customthe mixture evaporated to dryness in vacuo
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f86256d62a1c4dbfb05d7cc9aef022f1
Source dataset
uspto-grants-2007_06
Patent number
US07235549B2

Reaction notes

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