Dimethylformamide → HCID 53645791, compound

HRID 1387349Notes

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

Participants

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

customAfter completion of the reaction
extractionthe mixture was extracted with ether
dry with materialThe ether layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
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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