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

HRID 1671667

Reaktionsgleichung

Reaktionsgleichung von HRID 1671667
[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-c2c4fa95e446497a8f0cf6ec1b70a69e
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994338B2

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