Nitrogen → 4-Chloro-N-(3-chloro-quinoxalin-2-yl)-benzenesulfonamide

HRID 44204

Reaktionsgleichung

Reaktionsgleichung von HRID 44204
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[C:28](Cl)=[N:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.N#N>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:28]2[C:19]([Cl:18])=[N:20][C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:27]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 668244-Chlorobenzenesulfonamide

Produkt 1

HCID 23665104-Chloro-N-(3-chloro-quinoxalin-2-yl)-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-Chlorobenzenesulfonamide (1.92 g, 10 mmol) in anhydrous DMF (50 mL) was added solid potassium carbonate (1.38 g, 10 mmol) in one portion. The reaction mixture was stirred for 10 minutes, followed by the addition of 2,3-dichloroquinoxaline (1.99 g, 10 mmol). Heating the resultant mixture under refux conditions in an atmosphere of N2 for 2.5 h gave the desired product. The progress of the reaction was monitored by TLC using, hexanes/EtOAc 3:1. After cooling the reaction mixture is slowly added to a vigorously stirred aqueous solution of AcOH (1%, 500 mL). The desired product precipitates as grey crystals, which are filtered and dried overnight in desiccator. Yield 2.32 g, 66%; Rf=0.7 (hexanes/EtOAc 1:1); HPLC/MS: [M+H]+ m/z 354. 1H NMR: (DMSO-d6, 600 MHz) 7.68 (t, J=7.8 Hz, 1H), 7.72 (d, J=8.4 Hz, 2H), 7.78 (td, J=7.8 Hz, J=1.2 Hz, 1H), 7.89 (d, J=8.4 Hz, 2H), 8.19 (d, J=8.4 Hz, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-668aa4d5580442bc9eb04a23c849f206
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541415B2

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