Bromine → 2-Bromo-4-(1-methylpiperidin-4-ylidene)-9,10-dihydro-4H-3-thiabenzo[f]azulene hydrobromide
Reaction equation
[Br:1]Br.[CH3:3][N:4]1[CH2:9][CH2:8][C:7](=[C:10]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][CH2:16][C:15]3[CH:14]=[CH:13][S:12][C:11]2=3)[CH2:6][CH2:5]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[BrH:1].[Br:1][C:13]1[S:12][C:11]2[C:10](=[C:7]3[CH2:8][CH2:9][N:4]([CH3:3])[CH2:5][CH2:6]3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][CH2:16][C:15]=2[CH:14]=1Participants
5
Procedure
Bromine (0.52 mL, 10.2 mmol) was added dropwise to a chloroform (30 mL) solution of 4-(1-methylpiperidin-4-ylidene)-9,10-dihydro-4H-3-thiabenzo[f]azulene (3.0 g, 10.2 mmol) at 0° C. The mixture was stirred at room temperature for 2 days, and a saturated aqueous sodium bicarbonate solution was then added thereto to allow separation of an organic layer. The organic layer was washed with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvents were distilled off under a reduced pressure, and the residue was then purified by column chromatography (chloroform-methanol=9:1), to give 3.8 g (100%) of the captioned compound in the form of white crystals.
Workup
- customseparation of an organic layer
- washThe organic layer was washed with a saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvents were distilled off under a reduced pressure
- customthe residue was then purified by column chromatography (chloroform-methanol=9:1)
Sources & evidence
- ORD record
- ord-b28318d9c0e940dab87ae7356a888387
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377967B2
Reaction notes
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