Acetonitrile → HCID 638695, Verbindung

HRID 1350690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1350690
I.[CH3:2][NH:3][C:4](=[NH:7])[S:5][CH3:6].Br[C:9](=[CH:12][O:13]C(C)C)[CH:10]=[O:11].CC#N.C([O-])([O-])=O.[K+].[K+]>O>[CH3:2][N:3]1[C:9]([CH:10]=[O:11])=[CH:12][N:7]=[C:4]1[S:5][CH3:6].[CH3:2][N:3]1[CH:10]=[C:9]([CH:12]=[O:13])[N:7]=[C:4]1[S:5][CH3:6]

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 534166342-Bromo-3-isopropoxy-propenalHCID 178485204HCID 178485204, Verbindung

Produkt 2

HCID 638695HCID 638695, VerbindungHCID 210972441H-Imidazole-4-carboxaldehyde, 1-methyl-2-(methylthio)- (9CI)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a mixture of 2.65 g (11.4 mmol) of 1,2-dimethyl-isothiourea hydroiodide and 1.00 g (10.4 mmol) of 2-bromo-3-isopropoxy-propenal 8 mL of MeCN was added 1.58 g (11.4 mmol) of K2CO3 (Shilcrat, S. C. et al. J. Org. Chem., 1997, 62, 8449–8454). The mixture was stirred at 35° C. under N2 for 16 h, water (20 ml) was added, and the mixture was extracted with CH2Cl2 (200 mL). The extract was dried over MgSO4, filtered, concentrated, and chromatographed (0 to 100% EtOAc in hexanes) to provide 1.09 g of 3-methyl-2-methylsulfanyl-3H-imidazole-4-carbaldehyde and 284 mg of 1-methyl-2-methylsulfanyl-1H-imidazole-4-carbaldehyde.

Aufarbeitung

  1. extractionthe mixture was extracted with CH2Cl2 (200 mL)
  2. dry with materialThe extract was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (0 to 100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-aa359d021bd04eb1a0f5790763575632
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214802B2

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