Tetrahydrofuran → N-(2-methylamino-5-trifluoromethylpyridine-3-yl)-2-ethylsulfanyl-benzamide
Reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.C1COCC1.[CH2:19]([S:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25])[CH3:20].C(=O)([O-])O.[Na+]>O>[CH3:1][NH:2][C:3]1[C:8]([NH:9][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[S:21][CH2:19][CH3:20])=[CH:7][C:6]([C:10]([F:13])([F:11])[F:12])=[CH:5][N:4]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a mixture of N2-methyl-5-trifluoromethylpyridine-2,3-diamine (3.82 g) and THF (40 ml), 2-ethylsulfanylbenzoic acid chloride (4.42 g) was added, stirred at 50° C. for 2 hours, then stirred under reflux for hours. After the mixture was allowed to cool to room temperature, sodium hydrogen carbonate (1.85 g) was added thereto, and stirred at 50° C. for 2 hours. After the mixture was allowed to cool to room temperature, water was poured thereinto, and then the precipitated solid was collected by the filtration. The resulting solid was washed with water and hexane, and dried to give 7.15 g of N-(2-methylamino-5-trifluoromethylpyridine-3-yl)-2-ethylsulfanyl-benzamide (Compound ((1B)-19).
Workup
- additionwas added
- stirringstirred
- temperatureunder reflux for hours
- temperatureto cool to room temperature
- stirringstirred at 50° C. for 2 hours
- temperatureto cool to room temperature
- filtrationthe precipitated solid was collected by the filtration
- washThe resulting solid was washed with water and hexane
- customdried
Sources & evidence
- ORD record
- ord-fcf949da159c47eea476201a121308e8
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853238B2
Reaction notes
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