HCID 67359629, compound → 2-(3,4-Dimethoxy-5-nitrophenyl)-4-(2-(trifluoromethyl)pyridin-3-yl)-1,3,5-triazine
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.[F:21][C:22]([F:33])([F:32])[C:23]1[N:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](=[NH:27])[NH2:26]>>[CH3:19][O:18][C:9]1[CH:8]=[C:7]([C:6]2[N:26]=[C:25]([C:24]3[C:23]([C:22]([F:32])([F:21])[F:33])=[N:31][CH:30]=[CH:29][CH:28]=3)[N:27]=[CH:4][N:5]=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 2-(trifluoromethyl)nicotinimidamide (0.756 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 a 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 2-(3,4-dimethoxy-5-nitrophenyl)-4-(2-(trifluoromethyl)pyridin-3-yl)-1,3,5-triazine, 1.221 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 a 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-87f1abab238f45d1b580dff7b93bc794
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09446012B2
Reaction notes
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