Potassium tert-butoxide → HCID 22346862, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[N:21][OH:22])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2F)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>CN1CCCC1=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=3[O:22][N:21]=2)=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of N1-(4-bromophenyl)-2-fluoro-4-(trifluoromethyl)-1-benzeneamidoxime (2.25 g, 0.00598 mol) in N-methylpyrrolidinone (30 mL), potassium tert-butoxide (0.71 g, 0.00628 mol) was added and the resulting solution was heated at 100° C. under an atmosphere of nitrogen for 3 hours. The reaction mixture was cooled to ambient temperature, the solvent was removed under reduced pressure and the residue partitioned between saturated solution of sodium bicarbonate in water (50 mL) and ethyl acetate (50 mL). The organic phase was washed with brine, dried with magnesium sulfate and concentrated. The residue was suspended in cold n-heptane and the precipitate was collected by filtration and dried to yield N-(4-bromophenyl)-N-[6-(trifluoromethyl)benzo[d]isoxazol-3-yl]amine (1.75 g, 0.0049 mol) as an off-white solid.
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- customthe solvent was removed under reduced pressure
- customthe residue partitioned between saturated solution of sodium bicarbonate in water (50 mL) and ethyl acetate (50 mL)
- washThe organic phase was washed with brine
- dry with materialdried with magnesium sulfate
- concentrationconcentrated
- filtrationthe precipitate was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-c52296a4c4e64b0db7d2ae8d47c7d1d8
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06921763B2
Reaction notes
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