Methanol → 1-(3-Chlorophenyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazole-3-carboxylic Acid

HRID 541499Notes

Reaction equation

HRID 541499 reaction equation
C([O:3][C:4]([C:6]1[NH:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:7]=1)=[O:5])C.[Li+].[OH-].CO>O>[Cl:18][C:14]1[CH:13]=[C:12]([N:8]2[C:9](=[O:11])[NH:10][C:6]([C:4]([OH:5])=[O:3])=[N:7]2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 1360858841-(3-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-3-carboxylic acid ethyl ester

Product 1

HCID 1360859201-(3-Chlorophenyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazole-3-carboxylic AcidYield 0.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(3-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (200.0 mg, 747 mmol), LiOH (71.6 mg, 1.5 mmol) in water (2 mL), and MeOH (10.0 mL, 247 mmol) was stirred at room temperature overnight then concentrated. The residue was acidified with 1N HCl to pH 3-4, forming a precipitate, which was filtered, washed with water (2×5 mL), and dried in vacuo to yield the title compound (100.6 mg).

Workup

  1. concentrationthen concentrated
  2. customforming a precipitate, which
  3. filtrationwas filtered
  4. washwashed with water (2×5 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-30837eaf7ca34db890e4b302d9b6b6c4
Source dataset
uspto-grants-2014_10
Patent number
US08871792B2

Reaction notes

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