Bromine → 2-bromo-1H-imidazole-4,5-dicarbonitrile

HRID 1031166

Reaktionsgleichung

Reaktionsgleichung von HRID 1031166
[C:1]([C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]#[N:9])#[N:2].[Br:10]Br>[OH-].[Na+]>[Br:10][C:5]1[NH:4][C:3]([C:1]#[N:2])=[C:7]([C:8]#[N:9])[N:6]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 707294,5-Dicyanoimidazole

Produkt 1

HCID 27791482-bromo-1H-imidazole-4,5-dicarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

4,5-Dicyanoimidazole (23.6 g) was dissolved in sodium hydroxide solution (0.1N, 500 ml) with stirring and then bromine (36 ml) was added dropwise with stirring at room temperature. The mixture was stirred at room temperature overnight and the resulting solid was filtered, washed with water and dried to give 2-bromo-4,5-dicyanoimidazole m.p. 141°-144°. This compound (20 g) in dimethylformamide (100 ml) was added with stirring to a suspension of sodium hydride (80% dispersion in oil, 3.05 g) in dimethylformamide (100 ml) at room temperature. The mixture was cooled to 5° and chloromethyl 2-trimethylsilylethyl ether (18 ml) was added dropwise with stirring. This mixture was allowed to stand at room temperature overnight and was then poured into water and extracted with ethyl acetate. Evaporation of solvent gave an oil which was purified by column chromatography to give 1-(2-trimethylsilylethoxymethyl)-2-bromo-4,5-dicyano-1H-imidazole m.p.47°-52°. In a similar manner, the following were obtained: 1-benzyl- 2-bromo-4,5-dicyano-1H-imidazole, nD23 : 1.601, and 1-allyl-2-bromo-4,5-dicyano-1H-imidazole, m.p. 85°-87°.

Aufarbeitung

  1. stirringwith stirring at room temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. filtrationthe resulting solid was filtered
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a83dca654b1e40df83ea53ac3b3a7cf1
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05109012

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