HCID 67037361, compound → HCID 67036856, compound
Reaction equation
CN(/[CH:4]=[N:5]/[C:6](=O)[C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([O:16][CH3:17])=[C:9]([O:18][CH3:19])[CH:8]=1)C.[C:21]([C:24]1[C:25]([C:31]([F:34])([F:33])[F:32])=[N+:26]([O-:30])[CH:27]=[CH:28][CH:29]=1)(=[NH:23])[NH2:22]>>[CH3:19][O:18][C:9]1[CH:8]=[C:7]([C:6]2[N:5]=[CH:4][N:22]=[C:21]([C:24]3[C:25]([C:31]([F:32])([F:34])[F:33])=[N+:26]([O-:30])[CH:27]=[CH:28][CH:29]=3)[N:23]=2)[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]=1[O:16][CH3:17]Participants
3
Procedure
To a solution of (E)-N-((dimethylamino)methylene)-3,4-dimethoxy-5-nitrobenzamide (1.12 g, 4 mmol) ethanol (30 mL) was added 3-carbamimidoyl-2-(trifluoromethyl)pyridine 1-oxide (0.82 g, 4 mmol). The reaction mixture was heated to reflux for 5 hours. It was cooled to room temperature and the solvent was removed by evaporation. The residue was then dissolved in dichloromethane/isopropanol mixture (50 mL, 70:30) and the organic phase was washed with water, dried over anhydrous magnesium sulphate, filtered and evaporated. The crude product was recrystallized from ethanol to give 3-(4-(3,4-dimethoxy-5-nitrophenyl)-1,3,5-triazin-2-yl)-2-(trifluoromethyl)pyridine 1-oxide, 1.27 g (75%).
Workup
- temperatureThe reaction mixture was heated
- temperatureto reflux for 5 hours
- customthe solvent was removed by evaporation
- dissolutionThe residue was then dissolved in dichloromethane/isopropanol mixture (50 mL, 70:30)
- washthe organic phase was washed with water
- dry with materialdried over anhydrous magnesium sulphate
- filtrationfiltered
- customevaporated
- customThe crude product was recrystallized from ethanol
Sources & evidence
- ORD record
- ord-30a909349a6c43a7927ed5e58976c8df
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08907099B2
Reaction notes
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