3-Methoxyaniline → (3H-Imidazol-4-ylmethyl)-(3-methoxy-phenyl)-amine

HRID 2043346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2043346
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[CH:10]([C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)=O.[BH4-].[Na+]>CO>[N:15]1[CH:16]=[C:12]([CH2:10][NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 108243-MethoxyanilineHCID 764281H-Imidazole-4-carbaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 59728243(3H-Imidazol-4-ylmethyl)-(3-methoxy-phenyl)-amineAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of m-anisidine (0.91 ml, 8.12 mmol) in methanol (25 ml) was added 4-formylimidazole (0.86 g, 8.93 mmol). After stirring the mixture overnight at room temperature sodium borohydride (0.46 g, 12.2 mmol) was added. The reaction mixture was then concentrated in vacuo. The residue was purified using flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: methanol/dichloromethane 9:1) to yield a white solid (1.34 g, 18%); MS (ISP): 204.1 ([M+H]+).

Aufarbeitung

  1. additionwas added
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-c595360a005d4b628ed5b624a35b0594
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586617B2

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