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

HRID 1031166

反応式

HRID 1031166 の反応式
[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

参加物

4

反応物 2

HCID 24408BromineHCID 707294,5-Dicyanoimidazole

生成物 1

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

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-a83dca654b1e40df83ea53ac3b3a7cf1
出典データセット
uspto-grants-1992_04
特許番号
US05109012

関連ノート

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