Water → 1-(3,4-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

HRID 450509Notes

Reaction equation

HRID 450509 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([O:18]C)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([OH:18])=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 59583426Methyl 1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylate2×

Product 1

HCID 550298731-(3,4-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acidYield 84.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl 1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylate (Intermediate 7) (9 g, 0.03 mol) in methanol (200 mL) was added NaOH (2.4 g) and water. The mixture was stirred overnight. Water was added and the solvent was evaporated. The residue was extracted with DCM (twice). The aqueous phase was adjusted to pH=2 with a 2N HCl solution. The formed precipitate was filtered to give the title compound as a white solid (7.29 g, 84%). LC/MS: m/z 287 (M+H)+, Rt: 2.52 min.

Workup

  1. customthe solvent was evaporated
  2. extractionThe residue was extracted with DCM (twice)
  3. filtrationThe formed precipitate was filtered

Sources & evidence

ORD record
ord-548659da1dce47669512a10d76cd00fe
Source dataset
uspto-grants-2013_07
Patent number
US08486977B2

Reaction notes

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