Dimethylamine → N,N-dimethyl-4-nitro-2-(trifluoromethyl)aniline
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH3:15][NH:16][CH3:17].[H-].[Na+].O>O1CCCC1>[CH3:15][N:16]([CH3:17])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 1-floro-4-nitro-2-trifluoromethylbenzene (2.0 g) in tetrahydrofuran (20 mL) were added dimethyamine (0.64 g) and sodium hydride (0.34 g) at room temperature, and this mixture was stirred at 50° C. for 16 hours. This reaction mixture was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.94 g).
Workup
- extractionthis mixture was extracted with ethyl acetate
- washThis organic layer was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed under reduced pressure
- customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-5610ddc629e64e03850ebd0b4939866c
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003647B2
Reaction notes
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