Water → 4-(1H-1,2,3-triazol-1-yl)benzoic acid

HRID 1808876Notes

Reaction equation

HRID 1808876 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([C:10]#N)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[N:2]1.S(=O)(=O)(O)[OH:15].[OH2:19]>[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([C:10]([OH:15])=[O:19])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 97939604-(1H-1,2,3-Triazol-1-yl)benzonitrile2×

Product 1

HCID 226280454-(1H-1,2,3-triazol-1-yl)benzoic acidYield 81%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-(1H-1,2,3-triazol-1-yl)benzonitrile (200 mg, 1.175 mmol, prepared as described in WO 2006/067462 PCT/GB2005/005007 Page 57) in sulfuric acid (3 mL, 0.00 μmol)(50%, 3 ml) was refluxed at 120° C. for 4 h. Cooled down, diluted with water and adjusted pH to 4 with NaOH and Na2CO3, then extracted with ethyl acetate. After the solvent was removed, a white solid was obtained 4-(1H-1,2,3-triazol-1-yl)benzoic acid (180 mg, 0.952 mmol, 81% yield). 1H-NMR (DMSO-d6, 500 MHz): δ8.80 (1H, s), 8.13 (2H, d, J=8.55 Hz), 8.01 (2H, d, J=8.55 Hz), 7.98 (1H, s).

Workup

  1. temperatureCooled down
  2. extractionextracted with ethyl acetate
  3. customAfter the solvent was removed

Sources & evidence

ORD record
ord-aaf3cd4558d0436ebf0d5d997f2304c5
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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