Dimethylamine → N,N-dimethyl-4-nitro-2-(trifluoromethyl)aniline

HRID 73347

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

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-34e2102f3be048bb8fdf402940869913
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829040B2

Linked notes

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