Imidazole → 1-(3-nitrothiophen-2-yl)-1H-imidazole

HRID 2098201

Reaktionsgleichung

Reaktionsgleichung von HRID 2098201
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[C:7]1[S:8][CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13]>C(O)C>[N+:12]([C:11]1[CH:10]=[CH:9][S:8][C:7]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([O-:14])=[O:13]

Komponenten

4

Edukt 2

HCID 795ImidazoleHCID 2201862-Chloro-3-nitrothiophene

Produkt 1

HCID 208237541-(3-nitrothiophen-2-yl)-1H-imidazoleAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Imidazole (860 mg, 12.63 mmol) was added to a solution of 2-chloro-3-nitro-thiophene (1 g, 6.10 mmol) in abs. ethanol (20 mL). The reaction mixture was heated to reflux in a sealed tube for 3 days and then concentrated under reduced pressure. Purification by flash chromatography (silica, 25:75 ethyl/hexane) gave 1-(3-nitrothiophen-2-yl)-1H-imidazole (540 mg, 45%). See Erker, T. J. et al., J. Heterocylic. Chem. 39 (2002) 857-861. Method [3] m/z 195.9 (M+H); retention time=0.615.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux in a sealed tube for 3 days
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (silica, 25:75 ethyl/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e74c1fdce5cd4c44a12d2aa7174ee8cd
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450363B2

Verknüpfte Notizen

Wird geladen…