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Dimethylformamide → HCID 53645791, compound

HRID 1387349
Notes
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Reaction equation

HRID 1387349 reaction equation
CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=1.[CH3:23][O:24][N:25]=[C:26]([C:34]1[O:35][CH2:36][CH2:37][N:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33]>[OH-].[Na+]>[CH3:23][O:24][N:25]=[C:26]([C:34]1[O:35][CH2:36][CH2:37][N:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 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 14798
Sodium Hydroxide
Solvent

Conditions

Temperature
100 °C

Procedure

N,N-Dimethylformamide (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, aqueous in sodiumhydroxide solution (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. customAfter completion of the reaction
  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-148956bb24d241f0abd2753318a91f59
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06268312B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes