Dimethylformamide → HCID 54037022, compound

HRID 1004375Notes

Reaction equation

CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[F:12][C:13]([F:22])([F:21])[C:14]1[CH:15]=[CH:16][C:17](Cl)=[N:18][CH:19]=1.[CH3:23][O:24][N:25]=[C:26]([C:35]1[N:39]=[C:38]([CH3:40])[O:37][N:36]=1)[C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[OH:34]>CCOCC>[CH3:23][O:24][N:25]=[C:26]([C:35]1[N:39]=[C:38]([CH3:40])[O:37][N:36]=1)[C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[O:34][C:17]1[CH:16]=[CH:15][C:14]([C:13]([F:22])([F:21])[F:12])=[CH:19][N:18]=1

Participants

Conditions

Temperature: 110 °C

Procedure

N,N-Dimethylformamide (1 ml), potassium carbonate (0.10 g, 0.74 mmol) and 5-trifluoromethyl-2-chloropyridine (0.10 g, 0.56 mmol) were added to 5-chloro-2-hydroxyphenyl 5-methyl-1,2,4-oxadiazol-3-yl ketone O-methyloxime (0.10 g, 0.37 mmol), and the mixture was stirred at 110° C. for 2 hours. After completion of the reaction, ether (100 ml) was added, and the mixture was washed with saturated brine (80 ml) twice. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 5-chloro-2-(5-trifluoromethyl-2-pyridyloxy)phenyl 5-methyl-1,2,4-oxadiazol-3-yl ketone O-methyloxime (0.14 g, 91.7%) as a colorless oil.

Workup

additionwas added
washthe mixture was washed with saturated brine (80 ml) twice
dry with materialThe ether layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record: ord-7f3131d05e2b4aebb7d22f5c27ef587a
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06048885

Reaction notes

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