Water → N-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]-2-(trifluoromethyl)benzamide

In a solution of 151 mg of 2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-propyloxime and 86 mg of triethylamine in 4 ml of dichloromethane, 154 mg of 2-(trifluoromethyl)benzoyl chloride was added dropwise with stirring under cooling with ice, and after the addition, the mixture was stirred at room temperature for another 2 hours. After completion of the reaction, the reaction mixture was mixed with 10 ml of water and extracted with chloroform (30 ml×1), the resulting organic layer was washed with water (10 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 2:8 to 3:7) as the eluent to obtain 218 mg of the desired product as a pale yellow resinous substance.

1. temperatureunder cooling with ice
2. additionafter the addition
3. stirringthe mixture was stirred at room temperature for another 2 hours
4. customAfter completion of the reaction
5. extractionextracted with chloroform (30 ml×1)
6. washthe resulting organic layer was washed with water (10 ml×1)
7. dry with materialdried over saturated aqueous sodium chloride
8. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-c97955ef590e42a7aa823e60611fccb8

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434684B2