Hydrochloric Acid → HCID 13769460, compound

HRID 1382138Notes

Reaction equation

HRID 1382138 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([F:15])[C:12]([N:16]2[C:20](=[O:21])[N:19]([CH:22]([F:24])[F:23])[C:18]([CH3:25])=[N:17]2)=[CH:11][C:3]=1[O:4][CH:5]([CH3:10])[C:6]([O:8]C)=[O:7].[OH-].[K+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:14]=[C:13]([F:15])[C:12]([N:16]2[C:20](=[O:21])[N:19]([CH:22]([F:24])[F:23])[C:18]([CH3:25])=[N:17]2)=[CH:11][C:3]=1[O:4][CH:5]([CH3:10])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13822256HCID 13822256, compound

Product 1

HCID 13769460HCID 13769460, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A stirred mixture of 1.3 g (0.0034 mole) of methyl 2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionate and 1.0 g (0.018 mole) of potassium hydroxide in 15 mL of ethanol and 15 mL of water was heated at reflux for three hours. The mixture was allowed to cool to room temperature and stand for two days. The solvent was evaporated from the mixture leaving a solid. This solid was dissolved in water, and the solution was made acidic with concentrated hydrochloric acid. This solution was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and filtered. Evaporation of the solvent from the filtrate left 0.85 g of 2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionic acid as a solid (mp 50°-55° C.), Compound A2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. customThe solvent was evaporated from the mixture
  4. customleaving a solid
  5. extractionThis solution was extracted with methylene chloride
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customEvaporation of the solvent from the filtrate
  9. waitleft 0.85 g of 2-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]propionic acid as a solid (mp 50°-55° C.), Compound A2

Sources & evidence

ORD record
ord-448e8cf311f24c76b8ba42eae49d1048
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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