N-[1,1,1,3,3,3-Hexafluoro-2-(4-fluorophenyl)propan-2-yl]benzamide → HCID 15321202, compound
Reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)([NH:8]C(=O)C1C=CC=CC=1)[C:4]([F:7])([F:6])[F:5]>S(=O)(=O)(O)O.O.O>[F:7][C:4]([F:5])([F:6])[C:3]([NH2:8])([C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[C:2]([F:25])([F:24])[F:1]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
The benzamide (0.866 mg) was suspended in a mixture of 98% sulfuric acid/water (10:1, v/v, 11 mL) and heated to reflux (110° C.) for 6 hours. After diluting with water (15 mL), the solution was extracted thoroughly with diethylether (5×20 mL). The organic extracts were washed with 1N aqueous sodium hydrogen carbonate, with saturated aqueous sodium chloride and dried over sodium sulphate. The crude obtained after evaporating the solvent was purified by flash chromatography on silica gel (eluant: n-hexane/ethyl acetate 9:1) to afford 658 mg of the title compound.
Workup
- temperatureheated
- extractionthe solution was extracted thoroughly with diethylether (5×20 mL)
- washThe organic extracts were washed with 1N aqueous sodium hydrogen carbonate, with saturated aqueous sodium chloride
- dry with materialdried over sodium sulphate
- customThe crude obtained
- customafter evaporating the solvent
- customwas purified by flash chromatography on silica gel (eluant: n-hexane/ethyl acetate 9:1)
Sources & evidence
- ORD record
- ord-6e6524c7957a4967b621ba7dba8edebd
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06114345
Reaction notes
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