4-Methoxybenzenecarboximidamide → 2-(4-Methoxyphenyl)-4-(2-nitrophenyl)imidazole

HRID 378899

Reaktionsgleichung

Reaktionsgleichung von HRID 378899
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=O.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[NH:21])=[CH:18][CH:17]=1>C(#N)C>[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]2[NH:22][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N+:11]([O-:13])=[O:12])[N:21]=2)=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 2290744-MethoxybenzenecarboximidamideHCID 2440252-Bromo-2'-nitroacetophenone

Produkt 1

HCID 1784889232-(4-Methoxyphenyl)-4-(2-nitrophenyl)imidazoleAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 2-bromo-2′-nitroacetophenone (18 g), 4-methoxybenzamidine (20 g), and silica gel (20 g) in acetonitrile (500 ml) is heated at 40° C. for 24 hours. The reaction is evaporated and the residue put on a layer of silica gel and eluted with 50% ethyl acetate/hexane (1500 ml). The solution is evaporated under reduced pressure to approximately 250 ml and extracted with 5% HCl (3×250 ml). The combined aqueous solution is basified with K2CO3 and extracted with ethyl acetate (3×400 ml) to afford 2-(4-methoxyphenyl)-4-(2-nitrophenyl)-imidazole (17 g) as a dark yellow oil which is used in the next step without further purification.

Aufarbeitung

  1. customThe reaction is evaporated
  2. washthe residue put on a layer of silica gel and eluted with 50% ethyl acetate/hexane (1500 ml)
  3. customThe solution is evaporated under reduced pressure to approximately 250 ml
  4. extractionextracted with 5% HCl (3×250 ml)
  5. extractionextracted with ethyl acetate (3×400 ml)

Quellen und Nachweise

ORD-Eintrag
ord-ad59b6e86cc441af88a72d2c9740d441
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297252B1

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