Dimethylformamide → 2-(4-Chloro-3-trifluoromethyl-phenoxy)-3-methyl-5-nitro-pyridine
Reaction equation
CN(C=O)C.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[C:14]([F:17])([F:16])[F:15].Cl[C:19]1[C:24]([CH3:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:19]2[C:24]([CH3:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[CH:21][N:20]=2)=[CH:9][C:8]=1[C:14]([F:15])([F:16])[F:17]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A 250 ml two-necked round-bottomed flask equipped with a magnetic bar, a thermometer and a reflux condenser is charged with DMF (50 ml), 4-chloro-3-trifluoromethyl-phenol (4.6 g), 2-chloro-3-methyl-5-nitro-pyridine (4.0 g) and potassium carbonate (6.4 g). The reaction mixture is heated at 100° C. for 2.5 hours. After cooling the mixture to room temperature it is then poured into water (200 ml). The mixture is then extracted with ethylacetate (2×40 ml). The combined organic layers are dried over sodium sulfate, filtered and the solvent is removed in vacuo to obtain 6.10 g of the compound as yellow solid (MP: 95-97° C.).
Workup
- customA 250 ml two-necked round-bottomed flask equipped with a magnetic bar
- temperatureAfter cooling the mixture to room temperature it
- extractionThe mixture is then extracted with ethylacetate (2×40 ml)
- dry with materialThe combined organic layers are dried over sodium sulfate
- filtrationfiltered
- customthe solvent is removed in vacuo
Sources & evidence
- ORD record
- ord-ec3e4a12dcbb4c04bdd21fb7d1930330
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513286B2
Reaction notes
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