Hydrochloric Acid → 5-(3-Methanesulfonyl-[1,2,4]triazol-4-yl)-2-methoxy-benzoic acid

HRID 2230746Notes

Reaction equation

HRID 2230746 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[N:13][N:12]=[C:11]2[S:15]([CH3:18])(=[O:17])=[O:16])[CH:7]=[CH:6][C:5]=1[O:19][CH3:20].[OH-].[Li+].O.Cl>O1CCCC1>[CH3:18][S:15]([C:11]1[N:10]([C:8]2[CH:7]=[CH:6][C:5]([O:19][CH3:20])=[C:4]([CH:9]=2)[C:3]([OH:21])=[O:2])[CH:14]=[N:13][N:12]=1)(=[O:16])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 701493355-(3-Methanesulfonyl-[1,2,4]triazol-4-yl)-2-methoxy-benzoic acid methyl ester

Product 1

HCID 184644745-(3-Methanesulfonyl-[1,2,4]triazol-4-yl)-2-methoxy-benzoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stir a mixture of 5-(3-methanesulfonyl-[1,2,4]triazol-4-yl)-2-methoxy-benzoic acid methyl ester (1.0 g, 3.2 mmol), lithium hydroxide (0.042 g, 3.6 mmol), and 25% water in tetrahydrofuran (30 mL) at reflux overnight. Cool and add 1N hydrochloric acid (3.6 mL) dropwise via syringe. Concentrate to remove the tetrahydrofuran and collect the precipitate by vacuum filtration. Wash the filter cake twice with water and hexane, and dry in vacuo overnight to give 0.79 g of 5-(3-methanesulfonyl-[1,2,4]triazol-4-yl)-2-methoxy-benzoic acid as a solid.

Workup

  1. temperatureat reflux overnight
  2. temperatureCool
  3. concentrationConcentrate
  4. customto remove the tetrahydrofuran
  5. customcollect the precipitate
  6. filtrationby vacuum filtration
  7. washWash the filter cake twice with water and hexane
  8. customdry in vacuo overnight

Sources & evidence

ORD record
ord-ffbfbe83fb4148829e060adf685ef166
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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