Water → tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]carbamate

HRID 56018Notes

Reaction equation

HRID 56018 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:19][OH:20])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:33][C:34]([F:37])([F:36])[F:35])(=O)=O.O>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:9](=[N:19][O:20][CH2:33][C:34]([F:37])([F:36])[F:35])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 136987059tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]carbamate

Product 1

HCID 118071548tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-(2,2,2-trifluoroethoxyimino)ethyl]carbamateYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5.0 g of tert-butyl N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]carbamate in 16.0 ml of N,N-dimethylformamide, 4.3 g of potassium carbonate and 5.4 g of 2,2,2-trifluoroethyl trifluoromethanesulfonate were added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was mixed with 100 ml of water and extracted with ethyl acetate (100 ml×2), the resulting organic layers were combined, washed with water (50 ml×2) 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 0:10 to 3:7) as the eluent to obtain 4.8 g of the desired product as a pale yellow oil.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (100 ml×2)
  3. washwashed with water (50 ml×2)
  4. dry with materialdried over saturated aqueous sodium chloride
  5. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d0c9b7946e174fe78f9564fb0b5e5355
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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