Potassium Carbonate → N-(3-chloroquinoxalin-2-yl)-3-fluorobenzenesulfonamide

HRID 655619

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[Cl:12][C:13]1[C:22](Cl)=[N:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:12][C:13]1[C:22]([NH:11][S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)(=[O:9])=[O:10])=[N:21][C:20]2[C:15]([N:14]=1)=[CH:16][CH:17]=[CH:18][CH:19]=2

Komponenten

Reaktionsbedingungen

Temperatur: 135 °C

Versuchsvorschrift

3-fluorobenzenesulfonamide (250 mg, 1.4 mmol), 2,3-dichloroquinoxaline (284.1 mg, 1.4 mmol) and dry K2CO3 (198.4 mg, 1.4 mmol) are dissolved in dry DMF (0.8 ml) and heated up to 135° C. in a sealed tube for 2.5 h. When TLC confirms the completion of the reaction, the reaction mixture is cooled down to rt and quenched by addition of water (4 ml) and AcOH (0.03 ml). The residue obtained is triturated and the resulting solid is filtered and washed with water until neutral pH then dried under vacuum to afford 400 mg (83%) of the title compound as an off white solid. 1H NMR (DMSO-d6) δ 12.8-10.9 (br s, 1H), 8.05-7.62 (m, 7H), 7.54 (td, J=2.0, 8.5 Hz, 1H). HPLC (max plot) 94%; Rt 3.79 min. LC/MS: (ES+): 338.1, (ES−): 336.1.

Aufarbeitung

customthe completion of the reaction
temperaturethe reaction mixture is cooled down to rt
customquenched by addition of water (4 ml) and AcOH (0.03 ml)
customThe residue obtained
customis triturated
filtrationthe resulting solid is filtered
washwashed with water until neutral pH
customthen dried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-54ce079d10104fa0ad01baa3cd563bda
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08071597B2

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