2-(Methylthio)benzimidazole → 1-(4,6-Dimethoxypyrimidin-2-yl)-2-methylthiobenzimidazole

HRID 1368843

Reaktionsgleichung

Reaktionsgleichung von HRID 1368843
[CH3:1][S:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[H-].[Na+].CS([C:18]1[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=1)(=O)=O>CN(C)C=O>[CH3:27][O:26][C:20]1[CH:21]=[C:22]([O:24][CH3:25])[N:23]=[C:18]([N:7]2[C:6]3[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=3[N:4]=[C:3]2[S:2][CH3:1])[N:19]=1

Komponenten

5

Edukt 3

HCID 235392-(Methylthio)benzimidazoleHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine

Produkt 1

HCID 120569281-(4,6-Dimethoxypyrimidin-2-yl)-2-methylthiobenzimidazoleAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Methylthiobenzimidazole (0.50 g) was dissolved in dimethylformamide (10 ml), and sodium hydride (60% purity, oily) (0.13 g) was added thereto at room temperature. After stirring for 1 hour, 2-methylsulfonyl-4,6-dimethoxypyrimidine (0.67 g) was added at room temperature, followed by stirring for 8 hours. Ice water was added, followed by extraction with ethyl acetate, washing with a saturated sodium chloride aqueous solution and drying over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 0.80 g of the desired product as a white powder (m.p. 135-137° C.)

Aufarbeitung

  1. customat room temperature
  2. stirringby stirring for 8 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashing with a saturated sodium chloride aqueous solution
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1bc251bb25ee440c82588cd7ce58b165
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06576631B1

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