Water → Ethyl 1-phenyl-1H-1,2,3-triazole-4-carboxylate

HRID 1177927Notes

Reaction equation

HRID 1177927 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][C:11](=[O:17])[C:12](=[N+:15]=[N-:16])[CH:13]=O)[CH3:9].O>CCO>[CH2:8]([O:10][C:11]([C:12]1[N:15]=[N:16][N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=1)=[O:17])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 54182403Ethyl 2-diazo-2-formylacetate

Product 1

HCID 5270623Ethyl 1-phenyl-1H-1,2,3-triazole-4-carboxylateYield 87.41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aniline (143 mg, 1.5 mmol) was added to a solution of 2-diazo-3-oxo-propionic acid ethyl ester (200 mg, 1.4 mmol) and HAc (0.2 mL) in EtOH (0.5 mL) and stirring was at room temperature overnight. Reaction mixture was concentrated to get the residue. Cold water was then added, filtered the solid precipitated to afford 264 mg (87.41% Yield) of 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester. 1H NMR (CDCl3): δ 8.5 (s, 1H), 7.8 (d, 2H), 7.6-7.48 (m, 3H), 4.5 (q, 2H), 1.4 (t, 3H).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. customto get the residue
  4. filtrationfiltered the solid
  5. customprecipitated

Sources & evidence

ORD record
ord-98a15cba1383432390b8d331548503f0
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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