Benzene → N-(1-methoxy-2,2,2-trifluoroethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=[C:5]([C:20]([NH2:22])=[O:21])[CH:4]=1.O.[F:24][C:25]([F:29])([F:28])[CH:26]=[O:27].[CH:30]1C=CC=CC=1>>[CH3:30][O:27][CH:26]([NH:22][C:20]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[CH:11]=2)[N:6]=1)=[O:21])[C:25]([F:29])([F:28])[F:24]Participants
4
Procedure
4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide was dissolved in benzene and mixed with 0.36 g (0.0026×1.2 mol) of trifluoroacetaldehyde hydrate, followed by treating the obtained solution under reflux for about 5 hours. The reaction solution was concentrated and then distributed in ethyl acetate-saturated sodium bicarbonate water, followed by washing with saturated brine. The organic phase of the obtained solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.
Workup
- additionby treating the obtained solution
- temperatureunder reflux for about 5 hours
- concentrationThe reaction solution was concentrated
- washby washing with saturated brine
- dry with materialThe organic phase of the obtained solution was dried with anhydrous sodium sulfate
- concentrationconcentrated
- custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-e645bd9b7e22498b9d4dcd93fda32a2c
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06339045B1
Reaction notes
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