Hydrochloric Acid → 9-Bromo-8-hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile
Reaktionsgleichung
[Br:1][C:2]1[C:23]([O:24]C)=[CH:22][C:5]2[C:6]([CH3:21])([CH3:20])[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[C:16](=[O:17])[C:4]=2[CH:3]=1)=[CH:13][CH:12]=[C:11]([C:18]#[N:19])[CH:10]=4.C[O-].[Na+].C(S)CCCCCCCCCCC.Cl>CN1C(=O)CCC1>[Br:1][C:2]1[C:23]([OH:24])=[CH:22][C:5]2[C:6]([CH3:21])([CH3:20])[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[C:16](=[O:17])[C:4]=2[CH:3]=1)=[CH:13][CH:12]=[C:11]([C:18]#[N:19])[CH:10]=4Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 160 °C
Versuchsvorschrift
9-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound E3-1-1, 1.0 g, 2.53 mmol) was dissolved in NMP (10 mL), added with NaOMe (683 mg, 5 eq.) and 1-dodecanethiol (3.0 mL, 5 eq.), and stirred at 160° C. for 1 hr. The reaction solution was added to 0.5 N aqueous solution of hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were added with MeOH, and the solid remaining after dissolution was filtered to obtain the title compound (yellow powder, 1.88 g, 65%).
Aufarbeitung
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over sodium sulfate
- customThe drying agent was removed by filtration
- customthe residues obtained
- concentrationafter concentration under reduced pressure
- additionwere added with MeOH
- dissolutionafter dissolution
- filtrationwas filtered
Quellen und Nachweise
- ORD-Eintrag
- ord-4127e9db53a742c3af249ff3bec57c51
- Quelldatensatz
- uspto-grants-2015_09
- Patentnummer
- US09126931B2
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