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

HRID 2099151Notes

Reaction equation

HRID 2099151 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=[O:8])=[N+:2]=[N-:3].[C:14]([O:18][CH3:19])(=[O:17])[C:15]#[CH:16].O>CC(N(C)C)=O>[CH3:19][O:18][C:14]([C:15]1[N:3]=[N:2][N:1]([C:4]2[CH:5]=[C:6]([C:7]([OH:9])=[O:8])[CH:10]=[CH:11][C:12]=2[CH3:13])[CH:16]=1)=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 13536Methyl propiolateHCID 179730913-Azido-4-methylbenzoic acid2×

Product 1

HCID 587848831-(5-carboxy-2-methyl-phenyl)-1H-1,2,3-triazole-4-carboxylic acid methyl esterYield 62.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 1.11 g (6.27 mmol) of 3-azido-4-methyl benzoic acid (Compound 2) and 1.12 mL (12.5 mmol) of methyl propiolate, was stirred in 4.2 mL of DMA at 110° C. in a sealed tube overnight. The resulting brown solution was poured into water, and the resulting precipitate was filtered, and then recrystallized from EtOH/water to provide 1.02 g (62.3%) of 1-(5-carboxy-2-methyl-phenyl)-1H-1,2,3-triazole-4-carboxylic acid methyl ester as tan crystals. ESI MS (m/z 262, 100, M+1)

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customrecrystallized from EtOH/water

Sources & evidence

ORD record
ord-165d5df8488b4e7dac16929cf9864e2f
Source dataset
uspto-grants-2009_08
Patent number
US07569568B2

Reaction notes

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