Hydroxyamine hydrochloride → N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide
Reaction equation
[Cl:1][C:2]1[C:3]([C:9](=O)[CH2:10][NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[NH2:26][OH:27]>C(O)C>[Cl:1][C:2]1[C:3]([C:9](=[N:26][OH:27])[CH2:10][NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 2.8 g of N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamide in 19 ml of ethanol, 1.0 g of hydroxylamine hydrochloride was added, and the mixture was stirred at room temperature for 96 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, the resulting residue was mixed with 50 ml of water and extracted with ethyl acetate (50 ml×2), the resulting organic layers were combined, 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 5:95 to 50:50) as the eluent to obtain 2.8 g of the desired product as pale yellow crystals.
Workup
- customAfter completion of the reaction
- customthe solvent was evaporated under reduced pressure
- additionthe resulting residue was mixed with 50 ml of water
- extractionextracted with ethyl acetate (50 ml×2)
- dry with materialdried over saturated aqueous sodium chloride
- customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-db57420d47ee4361ab5ea2e8d7289783
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434684B2
Reaction notes
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