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

HRID 56010Notes

Reaction equation

HRID 56010 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][N:7]=1)=[O:5].[F:14][C:15]([F:26])([F:25])[C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Cl:12][C:11]1[C:6]([C:4](=[O:5])[CH2:3][NH:2][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[C:15]([F:14])([F:25])[F:26])=[N:7][CH:8]=[C:9]([Cl:13])[CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 1180715682-Amino-1-(3,5-dichloropyridin-2-yl)ethanone hydrochloride

Product 1

HCID 118071552N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamideYield 65.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 3.7 g of 2-amino-1-(3,5-dichloropyridin-2-yl)ethanone hydrochloride in 50 ml of ethyl acetate, 30 ml of water and 3.5 g of 2-(trifluoromethyl)benzoyl chloride were added, and 6.1 g of potassium carbonate in 30 ml of water was added dropwise with stirring under cooling with ice, and the mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, the reaction mixture was mixed with 20 ml of ethyl acetate, the resulting organic layer was collected, washed with water (20 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 6:4) as the eluent to obtain 3.8 g of the desired product as pale yellow crystals.

Workup

  1. additionwere added
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred at the same temperature for 30 minutes
  4. customAfter completion of the reaction
  5. customthe resulting organic layer was collected
  6. washwashed with water (20 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

Sources & evidence

ORD record
ord-eb0da34a5e534024886096c8607020a5
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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