Potassium Carbonate → HCID 53645791, compound

HRID 279463Notes

Reaction equation

HRID 279463 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1.[CH3:18][O:19][N:20]=[C:21]([C:29]1[O:30][CH2:31][CH2:32][N:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28].[OH-].[Na+]>CN(C=O)C>[CH3:18][O:19][N:20]=[C:21]([C:29]1[O:30][CH2:31][CH2:32][N:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 1361714202-hydroxyphenyl 2-oxazolin-2-yl ketone O-methyloxime

Product 1

HCID 53645791HCID 53645791, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

DMF (2.2 ml), potassium carbonate (210 mg, 1.5 mmol) and 2-chloro-5-trifluoromethylpyridine (220 mg, 1.2 mmol) were added to 2-hydroxyphenyl 2-oxazolin-2-yl ketone O-methyloxime (220 mg, 1.0 mmol), and the mixture was stirred at 100° C. for 2.5 hours. After completion of the reaction, 1N NaOH (100 ml) was added, and the mixture was extracted with ether. The ether layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(5-trifluoromethyl-2-pyridyloxy)phenyl 2-oxazolin-2-yl ketone O-methyloxime (190 mg, 52.1%) as an oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ether
  3. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-d72e46d10a5744c4b69dcd534f1cdbdd
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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