Hydrochloric Acid → 1-Phenyl-1H-1,2,3-triazole-4-carboxylic acid

HRID 1177928Notes

Reaction equation

HRID 1177928 reaction equation
[Li+].[OH-].C([O:5][C:6]([C:8]1[N:9]=[N:10][N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)=[O:7])C.O.Cl>C1COCC1.O>[C:13]1([N:11]2[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[N:9]=[N:10]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 5270623Ethyl 1-phenyl-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 5551941-Phenyl-1H-1,2,3-triazole-4-carboxylic acidYield 35.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

LiOH (80 mg, 1.9 mmol) was added to a stirred solution of 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (130 mg, 0.6 mmol) in THF:H2O (1:1, 4 mL), and the resulting mixture was stirred at room temperature for 45 min. The reaction mixture was concentrated under reduced pressure to get the residue. Cold water was then added and acidified it with 10% aqueous HCl, filtered the solid precipitated to afford 40 mg (35.4% yield) of 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid. 1H NMR (DMSO-d6): δ 13.4 (bs, 1H), 9.4 (s, 1H), 8.0 (d, 2H), 7.7 (t, 2H), 7.6 (t, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto get the residue
  3. filtrationfiltered the solid
  4. customprecipitated

Sources & evidence

ORD record
ord-04592faf6f01405cae737a2eedb0c230
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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