Bromine → 4-(2-Bromo-10H-9-oxa-3-thiabenzo[f]azulen-4-ylidene)-1-methyl-piperidine

HRID 389034Notes

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[O: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>[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[O:17][CH2:16][C:15]=2[CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Bromine (5 mL, 98 mmol) was added dropwise to a chloroform (300 mL) solution of 1-methyl-4-(10H-9-oxa-3-thiabenzo[f]azulen-4-ylidene)piperidine (19.3 g, 65.0 mmol) at 0° C. The mixture was stirred at 0° C. for 2 hours, and a saturated aqueous sodium hydrogencarbonate solution was then added thereto to allow the separation of an organic layer. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate, the solvents were then distilled off under a reduced pressure, and the residue was purified by column chromatography (chloroform:methanol=9:1). The crystals were formed from a petroleum ether, to give 11.2 g (46%) of the captioned compound.

Workup

customthe separation 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 then distilled off under a reduced pressure
customthe residue was purified by column chromatography (chloroform:methanol=9:1)
customThe crystals were formed from a petroleum ether

Sources & evidence

ORD record: ord-4a5ff1b0c3744990914209aa38dcc178
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377967B2

Reaction notes

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