Cesium carbonate → HCID 86586167, Verbindung

HRID 433587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 433587
Cl[CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH:7]=1.[NH:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH:21]=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:15][C:10]1[CH:9]=[C:8]([N:6]2[CH:7]=[C:3]([CH2:2][N:16]3[CH:20]=[CH:19][N:18]=[C:17]3[CH:21]=[O:22])[N:4]=[CH:5]2)[CH:13]=[CH:12][C:11]=1[Cl:14]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 249551H-imidazole-2-carbaldehydeHCID 234450324-Chloromethyl-1-(3,4-dichloro-phenyl)-1H-imidazole

Produkt 1

HCID 86586167HCID 86586167, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4-Chloromethyl-1-(3,4-dichloro-phenyl)-1H-imidazole (1.31 g, 5.0 mmol) was dissolved in DMF (10 ml), 2-imidazolecarboxaldehyde (0.48 g, 5.0 mmol) and cesium carbonate (0.82 g, 2.5 mmol) was added and the resulting mixture was stirred at 60° C. for 12 h. After evaporation of the solvent the residue was dissolved in AcOEt and washed with H2O. The organic phase was dried (Na2SO4), concentrated and chromatographed [silica, elution with gradient CH2Cl2 to 100% (CH2Cl2/MeOH=9:1)] to obtain 0.98 g (61%) of the title compound as an off-white solid. Mp. 130-131° C. (CH2Cl2/iPr2O), MS: m/e=320 (M+).

Aufarbeitung

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas dissolved in AcOEt
  3. washwashed with H2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customchromatographed
  7. wash[silica, elution with gradient CH2Cl2 to 100% (CH2Cl2/MeOH=9:1)]

Quellen und Nachweise

ORD-Eintrag
ord-ddadb30fbc9d4f52b3831f46ef27eae6
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06667335B2

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