Propiolic Acid → 1-Benzyl-1H-1,2,3-triazole-4-carboxylic acid

HRID 1982344Notes

Reaction equation

HRID 1982344 reaction equation
[CH2:1]([N:8]=[N+:9]=[N-:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([OH:15])(=[O:14])[C:12]#[CH:13]>CC(C)=O>[CH2:1]([N:8]1[CH:13]=[C:12]([C:11]([OH:15])=[O:14])[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10110Propiolic AcidHCID 12152Benzyl azide

Product 1

HCID 162277901-Benzyl-1H-1,2,3-triazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 84 milliliters (ml) of acetone and 35.8 grams (g) (269 mmoles) of benzyl azide, 19.3 g (276 mmoles) of propiolic acid was added by drop. The reaction mixture was stirred and heated to reflux overnight. After cooling to 0° C., 33.6 g (62%) of 1(2 or 3)-benzyl-1H-1,2,3-triazole-4-carboxylic acid precipitated from the reaction solution as white crystals. The structure was confirmed by nuclear magnetic resonance (n.m.r.) and infrared spectroscopy (I.R.).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. custom33.6 g (62%) of 1(2 or 3)-benzyl-1H-1,2,3-triazole-4-carboxylic acid precipitated from the reaction solution as white crystals

Sources & evidence

ORD record
ord-338750de855648ef8ac25a088de3bc9f
Source dataset
uspto-grants-1986_06
Patent number
US04596596

Reaction notes

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