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

HRID 655620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655620
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][C:14]1[CH:15]=[C:16]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Cl:12][C:11]1[C:2]([NH:23][S:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([CH3:13])[CH:15]=2)(=[O:21])=[O:22])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 74697m-Toluenesulphonamide

Produkt 1

HCID 4200291N-(3-chloroquinoxalin-2-yl)-3-methylbenzenesulfonamideAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A suspension of 2,3-dichloroquinoxaline (500 mg; 2.5 mmol; 1 eq), 3-methylbenzene sulfonamide (430.1 mg, 2.5 mmol, 1 eq.), dry K2CO3 (347.2 mg, 2.5 mmol, 1 eq.) in DMA (5 ml) is heated up at 170° C. in the microwave for 30 min under normal absorption. The solvent is evaporated to dryness. Water (20 ml) is added then AcOH until acidic pH. The residual suspension is left at 4° C. for 1 h and the precipitate formed is filtered off, washed with water until neutral, then ACN and dried under vacuum at 40° C. overnight, to afford 548.3 mg (65%) of the title compound. 1H NMR (DMSO-d6) δ 11.53 (brs, 1H), 7.99 (m, 2H), 7.87 (t, J=8.6 Hz, 2H), 7.77 (dt, J=1.5, 7.5 Hz, 1H), 7.67 (t, J=8.0 Hz, 1H), 7.56-7.43 (m, 2H), 2.42 (s, 3H). HPLC (max plot) 99%; Rt 3.70 min. LC/MS: (ES+): 334.2, (ES−): 332.2.

Aufarbeitung

  1. customThe solvent is evaporated to dryness
  2. additionWater (20 ml) is added
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washwashed with water until neutral, then ACN
  6. customdried under vacuum at 40° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-4f079997fb154167b50a705493d75b56
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071597B2

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