2-Butynoic acid → 1H-1,2,3-Triazole-4-carboxylic acid, 1-[(2-fluorophenyl)methyl]-

HRID 414092Notes

Reaction equation

HRID 414092 reaction equation
[F: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>[F: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 212826511-(Azidomethyl)-2-fluorobenzene

Product 1

HCID 212826151H-1,2,3-Triazole-4-carboxylic acid, 1-[(2-fluorophenyl)methyl]-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The starting material may be prepared as follows: A solution of 50 g (0.33 mole) of o-fluorobenzyl azide, 23.1 g (0.33 mole) of propinecarboxylic acid and 400 ml of toluene is stirred for 24 hours at 70° C. After the reaction mixture has cooled to room temperature, the precipitated product is filtered with suction and washed first with toluene and then with diethyl ether, affording 1-(o-fluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid with a melting point of 151° C. (dec.).

Workup

  1. customThe starting material may be prepared
  2. filtrationthe precipitated product is filtered with suction
  3. washwashed first with toluene

Sources & evidence

ORD record
ord-030f40ca22a2434c8b888b3c59e5d66c
Source dataset
uspto-grants-1988_12
Patent number
US04789680

Reaction notes

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