Methyl iodide → HCID 72944631, compound

HRID 1052925Notes

Reaction equation

HRID 1052925 reaction equation
[H-].[Na+].CI.[CH2:5]([S:7][C:8]1[CH:26]=[CH:25][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].[C:27](=O)(O)[O-].[Na+]>C1COCC1>[CH2:5]([S:7][C:8]1[CH:26]=[CH:25][CH:24]=[CH:23][C:9]=1[C:10]([N:12]([CH3:27])[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:15][N:14]=1)=[O:11])[CH3:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 72696793HCID 72696793, compound

Product 1

HCID 72944631HCID 72944631, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.03 g of 60% sodium hydride (oil-based) and 0.14 g of methyl iodide were added to a mixture of 0.15 g of 2-ethylsulfanyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide and 2 mL of THF, and the mixture was stirred at room temperature for 5 hours. A saturated aqueous sodium bicarbonate solution was poured 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 0.10 g of 2-ethylsulfanyl-N-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide (hereinafter, referred to as Compound of Present Invention 1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ddde53dd7e514c229206177247561e3c
Source dataset
uspto-grants-2016_07
Patent number
US09392791B2

Reaction notes

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