2-Butynoic acid → 1-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid

HRID 414087Notes

Reaction equation

HRID 414087 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][N:5]=[N+:6]=[N-:7].[C:12]([C:15]([OH:17])=[O:16])#[C:13]C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][N:5]1[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[N:7]=[N:6]1

Participants

4

Reactant 2

HCID 685352-Butynoic acidHCID 121946022-Chlorobenzyl azide

Product 1

HCID 212826341-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 16.75 g (100 mmol) of o-chlorobenzyl azide, 7.35 g (100 mmol) of propynecarboxylic acid and 200 ml of toluene is stirred for 24 hours at 50°. After being cooled to room temperature, the precipitated product is filtered off with suction and washed first with toluene and then with diethyl ether. In this manner there is obtained 1-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid having a melting point of 175° (with decomposition). After concentration of the filtrates by evaporation and washing the residue with a little toluene, 1-(o-chlorobenzyl)-1H-1,2,3-triazole-5-carboxylic acid having a melting point of 120° (with decomposition) remains.

Workup

  1. filtrationthe precipitated product is filtered off with suction
  2. washwashed first with toluene

Sources & evidence

ORD record
ord-bc8dce5f90de4e44b989e3e8b52e5b65
Source dataset
uspto-grants-1988_12
Patent number
US04789680

Reaction notes

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