Dimethylformamide → HCID 57974723, Verbindung

HRID 1864723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1864723
CN(C=O)C.[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].[N+:23]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Cl)([O-:25])=[O:24]>O>[N+:23]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)([O-:25])=[O:24]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 12078alpha-Chloro-m-nitrotolueneHCID 3168174-(1H-Imidazol-2-yl)-pyridine

Produkt 1

HCID 57974723HCID 57974723, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

DMF (20 mL) is added to 4-(1H-Imidazol-2-yl)-pyridine (930 mg, 6.4 mmol), sodium carbonate (1.92 g, 20 mmol), and 3-nitrobenzyl chloride (1.71 g, 10 mmol) and the mixture is warmed to 50° C. for 4 h. Water (100 mL) is added and the corresponding mixture is extracted with EtOAc (100 mL), dried over anhydrous sodium sulfate, and crude solution is concentrated under reduced pressure. The organics are dissolved in DCM and filtered through a plug of silica eluting first with DCM, and then washing with 20% MeOH:80% DCM to afford 4-[1-(3-Nitro-benzyl)-1H-imidazol-2-yl]-pyridine as an off-white solid.

Aufarbeitung

  1. extractionthe corresponding mixture is extracted with EtOAc (100 mL)
  2. dry with materialdried over anhydrous sodium sulfate, and crude solution
  3. concentrationis concentrated under reduced pressure
  4. dissolutionThe organics are dissolved in DCM
  5. filtrationfiltered through a plug of silica eluting first with DCM
  6. washwashing with 20% MeOH

Quellen und Nachweise

ORD-Eintrag
ord-8225807d2eca4f4dadf558460b50365f
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625931B2

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