Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(Trifluoromethyl)benzoyl chloride | HCID 67561 | — |
| Reactant | 2-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone-O-ethyloxime | HCID 118071573 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 131736890 | HCID 131736890 | 71.2% |
Reaction Steps
To a solution of 47 mg of 2-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone-O-ethyloxime and 25 mg of triethylamine in 2 ml of dichloromethane, 31 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 1 hour. After completion of the reaction, the reaction mixture was mixed with 2 ml of water and extracted with dichloromethane (2 ml×1), the resulting organic layer was 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 preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.) using ethyl acetate-hexane (with a gradient of from 2:18 to 5:15) as the eluent to obtain 48 mg of the desired product as a colorless resinous substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09434684B2 |
|---|
| Source dataset | uspto-grants-2016_09 |
|---|
| ORD ID | ord-c5c7f8d304924c51a1f26ba772adab90 |
|---|
| Source note | uspto-grants-2016_09 |
|---|