Hydrochloric Acid → HCID 19436753, compound

HRID 260960Notes

Reaction equation

HRID 260960 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([C:17]2[C:21]([Cl:22])=[C:20]([C:23]([F:26])([F:25])[F:24])[N:19]([CH3:27])[N:18]=2)=[CH:12][C:3]=1[O:4][CH:5]([CH3:11])[C:6]([O:8]CC)=[O:7].[OH-].[Na+].Cl>O.O1CCOCC1>[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([C:17]2[C:21]([Cl:22])=[C:20]([C:23]([F:25])([F:26])[F:24])[N:19]([CH3:27])[N:18]=2)=[CH:12][C:3]=1[O:4][CH:5]([CH3:11])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86747523HCID 86747523, compound

Product 1

HCID 19436753HCID 19436753, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a slurry of 1.4 g (3.3 mmole) 2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4 -fluorophenoxy)-propanoic acid, ethyl ester in 50 mL water and 30 mL 1,4-dioxane was added 1.3 mL (3.3 mmole) of a 10% NaOH solution. After 30 minutes, the solution was cooled and the pH adjusted to 3 with concentrated HCl. The reaction mixture was extracted with diethyl ether. The ether solution was washed with water, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was recrystallized from methylcyclohexane to give 1.3 g (100%) of 2-(2-chloro-5-(4-chloro-1-methyl-5-(tri-fluoromethyl)-1H-pyrazol-3-yl)-4-fluorophenoxy)-propanoic acid as a white solid, mp 150°-151° C.

Workup

  1. temperaturethe solution was cooled
  2. extractionThe reaction mixture was extracted with diethyl ether
  3. washThe ether solution was washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-62cca1d0ec8a405d8a06cf2987c62497
Source dataset
uspto-grants-1996_06
Patent number
US05530126

Reaction notes

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