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

HRID 1031166

반응식

HRID 1031166 반응식
[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

참가 물질

4

반응물 2

HCID 24408BromineHCID 707294,5-Dicyanoimidazole

생성물 1

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

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-a83dca654b1e40df83ea53ac3b3a7cf1
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05109012

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