Ethanol → 2-Phenyl-2H-1,2,3-triazole-4,5-dicarboxylic acid

HRID 2298015Notes

Reaction equation

HRID 2298015 reaction equation
CC1[C:3]([C:13]([OH:15])=[O:14])=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[OH-:16].[Na+].[O-][Mn](=O)(=O)=O.[K+].[CH2:24]([OH:26])[CH3:25]>O>[C:7]1([N:5]2[N:6]=[C:25]([C:24]([OH:16])=[O:26])[C:3]([C:13]([OH:15])=[O:14])=[N:4]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 5199365-methyl-2-phenyl-2H-1,2,3-triazole-4-carboxylic acid

Product 1

HCID 222680202-Phenyl-2H-1,2,3-triazole-4,5-dicarboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 5-methyl-2-phenyl-2H-1,2,3-triazole-4-carboxylic acid (10.2 g, 50 mmol) and NaOH (17.6 g, 440 mmol) in water (375 mL) at 23° C. was treated with KMnO4 (30.8 g, 195 mmol). The resulting solution was heated at reflux for 17 h, cooled to 23° C. and treated with ethanol (50 mL). The resulting mixture was filtered to remove MnO2. The filtrate was acidified with HCl (conc.) to pH 1. The resulting white solid was collected by filtration. The filtrate was concentrated to half volume and more solid was collected by filtration. The two combined batches of solid were dried in vacuo to afford 11.1 g (95%) of 2-phenyl-2H-1,2,3-triazole-4,5-dicarboxylic acid.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 17 h
  3. filtrationThe resulting mixture was filtered
  4. customto remove MnO2
  5. filtrationThe resulting white solid was collected by filtration
  6. concentrationThe filtrate was concentrated to half volume and more solid
  7. filtrationwas collected by filtration
  8. customThe two combined batches of solid were dried in vacuo

Sources & evidence

ORD record
ord-0d6a21bd443f487f8a5ceaa1c858b0c5
Source dataset
uspto-grants-2002_12
Patent number
US06492401B1

Reaction notes

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