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

HRID 2230744Notes

Reaction equation

HRID 2230744 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[N:13][N:12]=[C:11]2[S:15][CH3:16])[CH:7]=[CH:6][C:5]=1[O:17][CH3:18].[OH-].[Li+].O.Cl>O1CCCC1>[CH3:18][O:17][C:5]1[CH:6]=[CH:7][C:8]([N:10]2[CH:14]=[N:13][N:12]=[C:11]2[S:15][CH3:16])=[CH:9][C:4]=1[C:3]([OH:19])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 701482672-Methoxy-5-(3-methylsulfanyl-[1,2,4]triazol-4-yl)-benzoic acid methyl ester

Product 1

HCID 184647022-Methoxy-5-(3-methylsulfanyl-[1,2,4]triazol-4-yl)-benzoic acidYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stir a mixture of 2-methoxy-5-(3-methylsulfanyl-[1,2,4]triazol-4-yl)-benzoic acid methyl ester (0.28 g, 3.5 mmol), lithium hydroxide (0.041 g, 3.8 mmol), and 25% water in tetrahydrofuran (20 mL) overnight. Add 1N hydrochloric acid (3.9 mL) dropwise to pH 3. 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 0.89 g of 2-methoxy-5-(3-methylsulfanyl-[1,2,4]triazol-4-yl)-benzoic acid as a solid.

Workup

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

Sources & evidence

ORD record
ord-80c074de2c96405881f1ea29644ce28a
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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