Methyl iodide → 2-ethylsulfanyl-N-methyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide

HRID 1052928Notes

Reaction equation

HRID 1052928 reaction equation
[H-].[Na+].CI.[CH2:5]([S:7][C:8]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:9]=1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=1)=[O:11])[CH3:6].[CH2:31]1COCC1>O>[CH2:5]([S:7][C:8]1[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=[CH:23][C:9]=1[C:10]([N:12]([CH3:31])[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][N:14]=1)=[O:11])[CH3:6]

Participants

6

Reactant 4

HCID 6328Methyl iodide3×HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 1180350972-ethylsulfanyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyri din-2-yl)-benzamide

Product 1

HCID 729447402-ethylsulfanyl-N-methyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.12 g of 60% sodium hydride (oil-based) and 0.56 g of methyl iodide were added to a mixture of 0.78 g of 2-ethylsulfanyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyri din-2-yl)-benzamide and 5 mL of THF, and the mixture was stirred at room temperature for 2 hours. 1 g of methyl iodide was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hours. 1 g of methyl iodide was further added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, 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 0.59 g of 2-ethylsulfanyl-N-methyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide (hereinafter, referred to as Compound of Present Invention 2).

Workup

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

Sources & evidence

ORD record
ord-2bcd2941d04243a2a6960c886e5891a2
Source dataset
uspto-grants-2016_07
Patent number
US09392791B2

Reaction notes

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