Potassium Hydroxide → HCID 22267595, compound

HRID 488792Notes

Reaction equation

HRID 488792 reaction equation
[C:1]1([N:7]2[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([C:16]([O:18]C)=[O:17])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CO>[CH3:15][O:14][C:12]([C:10]1[C:9]([C:16]([OH:18])=[O:17])=[N:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:11]=1)=[O:13]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 143448404,5-Dimethyl 2-phenyl-2H-1,2,3-triazole-4,5-dicarboxylate

Product 1

HCID 22267595HCID 22267595, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of dimethyl 2-phenyl-2H-1,2,3-triazole-4,5-dicarboxylate (0.522 g, 2.00 mmol) in methanol (40 mL) at 23° C. was treated with a solution of KOH (0.236 g, 4.20 mmol) in methanol (5 mL). The resulting solution was stirred at 23° C. for 17 h and partitioned between NaHCO3 (sat. aq. sol.) and ether. The aqueous layer was washed with ether and acidified carefully to pH 1 with HCl (conc.). The resulting mixture was extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by radial chromatography (2 mm plate, CH2Cl2-methanol-acetic acid 90:10:1) to afford 0.42 g (85%) of 5-methoxycarbonyl-2-phenyl-2H-1,2,3-triazole-4-carboxylic acid.

Workup

  1. custompartitioned between NaHCO3 (sat. aq. sol.) and ether
  2. washThe aqueous layer was washed with ether
  3. extractionThe resulting mixture was extracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by radial chromatography (2 mm plate, CH2Cl2-methanol-acetic acid 90:10:1)

Sources & evidence

ORD record
ord-2a56b3910f9f4449a08c581de20420f9
Source dataset
uspto-grants-2005_12
Patent number
US06974813B2

Reaction notes

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