Acetone → N-ethyl-2-ethylsulfanyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide
Reaction equation
C(=O)([O-])[O-].[K+].[K+].CI.[CH2:9]([S:11][C:12]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:13]=1[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1)=[O:15])[CH3:10].C(=O)(O)[O-].[Na+].[CH3:40][C:41](C)=O>CN(C=O)C>[CH2:40]([N:16]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][N:18]=1)[C:14](=[O:15])[C:13]1[CH:27]=[CH:28][C:29]([C:31]([F:34])([F:32])[F:33])=[CH:30][C:12]=1[S:11][CH2:9][CH3:10])[CH3:41]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
0.21 g of potassium carbonate and 0.78 g of methyl iodide were added to a mixture of 0.39 g of 2-ethylsulfanyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide 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, and the mixture was stirred at 60° C. for 1 hour. A saturated aqueous sodium bicarbonate solution was added to the cooled 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 0.31 g of N-ethyl-2-ethylsulfanyl-4-trifluoromethyl-N-(5-trifluoromethyl-pyridin-2-yl)-benzamide (hereinafter, referred to as Compound of Present Invention 4).
Workup
- stirringthe mixture was stirred at 60° C. for 1 hour
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b193ce413afd4b718526a15a6fcf673c
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09392791B2
Reaction notes
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