Methyl iodide → 3,4-dimethoxy-N-[4-(3-nitrophenyl)thiazol-2-yl]-N-(methyl)benzenesulfonamide

HRID 2370978

Reaktionsgleichung

Reaktionsgleichung von HRID 2370978
[C:1](=O)([O-])[O-].[K+].[K+].CI.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([S:19]([NH:22][C:23]2[S:24][CH:25]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=3)[N:27]=2)(=[O:21])=[O:20])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]>C(#N)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([S:19]([N:22]([C:23]2[S:24][CH:25]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=3)[N:27]=2)[CH3:1])(=[O:21])=[O:20])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 52823373,4-Dimethoxy-N-(4-(3-nitrophenyl)-2-thiazolyl)benzenesulfonamide

Produkt 1

HCID 248124223,4-dimethoxy-N-[4-(3-nitrophenyl)thiazol-2-yl]-N-(methyl)benzenesulfonamideAusbeute 6,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Anhydrous potassium carbonate (0.204 g, 14.8 mmol), and methyl iodide (0.209 g, 14.8 mmol) were added to a stirred solution of 3,4-dimethoxy-N-(4-(3-nitrophenyl)thiazol-2-yl)benzenesulfonamide (0.250 g, 5.94 mmol) in acetonitrile (10 mL) under a nitrogen atmosphere at room temperature. After 2 h, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed in vacuo. The crude reaction mixture was subjected to purification by column chromatography on silica gel. Elution with an ethyl acetate-hexane mixture (20:80) gave 3,4-dimethoxy-N-[4-(3-nitrophenyl)thiazol-2-yl]-N-(methyl)benzenesulfonamide (0.175 g) as a white colored solid.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe crude reaction mixture
  6. customwas subjected to purification by column chromatography on silica gel
  7. washElution with an ethyl acetate-hexane mixture (20:80)

Quellen und Nachweise

ORD-Eintrag
ord-5c07c5f5bcef40f6b2e5863ce75683f5
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710237B2

Verknüpfte Notizen

Wird geladen…