Water → HCID 118071560, compound

HRID 56053Notes

Reaction equation

HRID 56053 reaction equation
[Cl:1][C:2]1[C:3]([C:12](=[N:27][OH:28])[CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:36]([CH3:38])[CH3:37].O>CN(C)C=O>[Cl:1][C:2]1[C:3](/[C:12](=[N:27]/[O:28][CH:36]([CH3:38])[CH3:37])/[CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:24])([F:25])[F:23])=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 136987057HCID 136987057, compound

Product 1

HCID 118071560HCID 118071560, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 20.00 g of N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide and 19.48 g of potassium carbonate in 105 ml of N,N-dimethylformamide, 10.38 g of 2-iodopropane was added, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was mixed with 200 ml of water and extracted with ethyl acetate (100 ml×3), the resulting organic layers were combined, washed with water (100 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 1:9 to 3:7) as the eluent to obtain 11.00 g of the desired product as white crystals.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (100 ml×3)
  4. washwashed with water (100 ml×1)
  5. dry with materialdried 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-9f2035fb394b48218f4d461dba54ade4
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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