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

HRID 56012Notes

Reaction equation

HRID 56012 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:24][OH:25])[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.C(=O)([O-])[O-].[K+].[K+].I[CH:33]([CH3:35])[CH3:34].O>CN(C)C=O>[Cl:1][C:2]1[C:3](/[C:9](=[N:24]/[O:25][CH:33]([CH3:35])[CH3:34])/[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:20])([F:22])[F:21])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 136987066N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide

Product 1

HCID 118071529(Z)-N-[2-(3,5-dichloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamideYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 300 mg of N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide and 315 mg of potassium carbonate in 3 ml of N,N-dimethylformamide, 195 mg of 2-iodopropane was added, and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was mixed with 20 ml of water and extracted with ethyl acetate (10 ml×2), the resulting organic layers were combined, washed with water (10 ml×2), 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 silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 258 mg of the desired product as white crystals.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (10 ml×2)
  4. washwashed with water (10 ml×2)
  5. dry with materialthe resulting organic layer was dried over saturated aqueous sodium chloride
  6. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ed229e2b0ff549e199ff0d575d3a1513
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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