Potassium Carbonate → N-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

HRID 56020Notes

Reaction equation

HRID 56020 reaction equation
Cl.[F:2][C:3]([F:19])([F:18])[CH2:4][O:5][N:6]=[C:7]([C:10]1[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][N:11]=1)[CH2:8][NH2:9].[F:20][C:21]([F:32])([F:31])[C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25].C(=O)([O-])[O-].[K+].[K+]>O.ClCCl>[Cl:16][C:15]1[C:10]([C:7](=[N:6][O:5][CH2:4][C:3]([F:18])([F:2])[F:19])[CH2:8][NH:9][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[C:21]([F:20])([F:31])[F:32])=[N:11][CH:12]=[C:13]([Cl:17])[CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 1180715562-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-(2,2,2-trifluoroethyl)oxime hydrochloride

Product 1

HCID 118071540N-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]-2-(trifluoromethyl)benzamideYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 2.0 g of 2-amino-1-(3,5-dichloropyridin-2-yl)ethanone-O-(2,2,2-trifluoroethyl)oxime hydrochloride in 12.0 ml of water, 1.4 g of 2-(trifluoromethyl)benzoyl chloride in 12.0 ml of dichloromethane and 2.4 g of potassium carbonate were added at room temperature with stirring, and the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the resulting organic layer was collected and dried over 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 2.6 g of the desired product as a pale yellow resinous substance.

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hours
  2. customAfter completion of the reaction
  3. customthe resulting organic layer was collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d4646a71b79e425486ddaa83f425145d
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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