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

HRID 2082398

Reaction equation

HRID 2082398 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°.

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-83aa55ff9f6c4583be32fc756e6b97d9
Source dataset
uspto-grants-1993_02
Patent number
US05189053

Linked notes

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