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

HRID 1031166

Reaction equation

HRID 1031166 reaction equation
[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

Participants

4

Reactant 2

HCID 24408BromineHCID 707294,5-Dicyanoimidazole

Product 1

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

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-a83dca654b1e40df83ea53ac3b3a7cf1
Source dataset
uspto-grants-1992_04
Patent number
US05109012

Linked notes

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