Iodoethane → N-ethyl-3-ethylsulfanyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide

HRID 713659Notes

Reaction equation

HRID 713659 reaction equation
[CH2:1](I)[CH3:2].[CH2:4]([S:6][C:7]1[C:8]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=2)=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:5].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>O.CN(C=O)C.CC(C)=O>[CH2:1]([N:15]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][N:17]=1)[C:13](=[O:14])[C:8]1[C:7]([S:6][CH2:4][CH3:5])=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:2]

Participants

8

Reactant 4

HCID 6340Iodoethane2×HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 1182059283-ethylsulfanyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide

Product 1

HCID 118205941N-ethyl-3-ethylsulfanyl-N-(5-trifluoromethylpyridin-2-yl)picolinamideYield 48.9%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.78 g of ethyl iodide was added to a mixture of 0.32 g of 3-ethylsulfanyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide (Compound of Present Invention 2), 0.21 g of potassium carbonate and 3 mL of acetone, and the mixture was stirred at room temperature for 1 hour. 3 mL of DMF was added to the reaction mixture, the mixture was stirred at 60° C. for 1 hour and then cooled to room temperature, and 1.0 g of ethyl iodide was added and then the mixture was stirred at 60° C. for 2 hours. Water and a saturated aqueous sodium bicarbonate solution were poured to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.17 g of N-ethyl-3-ethylsulfanyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide (hereinafter, referred to as Compound of Present Invention 26).

Workup

  1. stirringthe mixture was stirred at 60° C. for 1 hour
  2. temperaturecooled to room temperature
  3. stirringthe mixture was stirred at 60° C. for 2 hours
  4. temperaturecooled to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce48986392ba4961a6542fa149afc440
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

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