Hydrochloric Acid → HCID 178468330, compound
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].Cl.[N:13]([O-])=O.[Na+].[Br:17][C:18]1[CH:22]=[CH:21][O:20][C:19]=1[C:23](=[O:28])[CH2:24][C:25](=[O:27])[CH3:26].C([O-])(=O)C.[Na+]>O.CO>[Br:17][C:18]1[CH:22]=[CH:21][O:20][C:19]=1[C:23](=[O:28])[C:24](=[N:13][NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)[C:25](=[O:27])[CH3:26]Participants
8
Procedure
To a mixture of 3-(trifluoromethyl)aniline (0.500 mL) and 6M hydrochloric acid (4 mL) was added dropwise a solution of sodium nitrite (0.345 g) in water (1 mL) at 0° C., and the mixture was stirred for 15 min. The obtained aqueous solution was added to a suspension, which was cooled to 0° C., of 1-(3-bromofuran-2-yl)butane-1,3-dione (0.924 g) and sodium acetate (1.97 g) in methanol (10 mL). The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (1.59 g).
Workup
- additionThe obtained aqueous solution was added to a suspension, which
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-10a5698f56674a338e20275f90d92abb
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150588B2
Reaction notes
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