Sodium Hydroxide → 1-(3,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid

HRID 222368Notes

Reaction equation

HRID 222368 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH:14]=[C:13]([C:15]([O:17]CC)=[O:16])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59583668Ethyl 1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazole-4-carboxylate2×

Product 1

HCID 595836511-(3,4-dichlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazole-4-carboxylate (Intermediate 10) (1.5 g, 5 mmol) and a 1N NaOH solution (7.5 mL, 1.5 eq) in ethanol (50 mL) was stirred at reflux for 48 hours. The solvent was evaporated and the residue was acidified with a 1N HCl solution (15 mL). The precipitate formed was filtered, washed with water and dried to give the title compound as a white solid (1.25 g, 92%). LC/MS: m/z 272 (M+H)+. Rt: 2.05 min.

Workup

  1. temperatureat reflux for 48 hours
  2. customThe solvent was evaporated
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-c5ccb9ba77314d1782006b9b322d8b21
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Reaction notes

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