Methyl 4-fluorobenzoylacetate → 1-(5-Chloro-2,4-dimethoxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid

HRID 12439

Reaction equation

HRID 12439 reaction equation
[N:1]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][CH3:12])=[CH:6][C:5]=1[O:13][CH3:14])=[N+:2]=[N-:3].C[O:16][C:17](=[O:28])[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=O.[O-]CC.[Na+]>CCO>[Cl:10][C:8]1[C:7]([O:11][CH3:12])=[CH:6][C:5]([O:13][CH3:14])=[C:4]([N:1]2[C:19]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)=[C:18]([C:17]([OH:28])=[O:16])[N:3]=[N:2]2)[CH:9]=1

Participants

5

Reactant 3

HCID 579425Methyl 4-fluorobenzoylacetateHCID 2723922Sodium ethoxideHCID 587310171-Azido-5-chloro-2,4-dimethoxybenzene

Product 1

HCID 587310181-(5-Chloro-2,4-dimethoxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Azido-5-chloro-2,4-dimethoxy-benzene (0.4 g, 1.9 mmol), 3-(4-Fluoro-phenyl)-3-oxo-propionic acid methyl ester (0.42 g, 2.2 mmol) and sodium ethoxide in EtOH (70 mg of sodium in 15 mL EtOH) were refluxed for 3 hours. During the reaction, the solution turned brown from dark green. After that, EtOH was evaporated off and the resulting oil was dried in vacuum. Trituration with ether (15 mL) gave light brown solids, which were removed by filtration and washed with ether. The solids then re-dissolved in CHCl3 and filtered. After evaporation of the solvent, light brown solids were obtained (0.35 g, 50%).

Workup

  1. customDuring the reaction
  2. customAfter that, EtOH was evaporated off
  3. customthe resulting oil was dried in vacuum
  4. customTrituration with ether (15 mL) gave light brown solids, which
  5. customwere removed by filtration
  6. washwashed with ether
  7. dissolutionThe solids then re-dissolved in CHCl3
  8. filtrationfiltered
  9. customAfter evaporation of the solvent
  10. customlight brown solids were obtained (0.35 g, 50%)

Sources & evidence

ORD record
ord-7a8b9422f4634db6947a7b29d86ba228
Source dataset
uspto-grants-2010_06
Patent number
US07728016B2

Linked notes

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