Water → 9-Benzyl-3,6-dicyanocarbazole

HRID 460876ノート

反応式

HRID 460876 の反応式
[H-].[Na+].[C:3]([C:5]1[CH:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([C:18]#[N:19])=[CH:12][CH:11]=3)#[N:4].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:20]([N:9]1[C:10]2[CH:11]=[CH:12][C:13]([C:18]#[N:19])=[CH:14][C:15]=2[C:16]2[C:8]1=[CH:7][CH:6]=[C:5]([C:3]#[N:4])[CH:17]=2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 107751409H-carbazole-3,6-dicarbonitrile

生成物 1

HCID 213948759-Benzyl-3,6-dicyanocarbazole収率 79.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A slurry of sodium hydride (50% in oil, 960 mg) in 100 ml of dimethylformamide is treated with 3,6-dicyanocarbazole (4.34 g, see Example 1) and heated at 110° C for two hours. The reaction mixture is then treated dropwise with benzylbromide (3.42 g) and heated at 110° C for an additional 18 hours. The reaction mixture is poured into water and extracted several times with dichloromethane. The combined dichloromethane extracts are dried over sodium sulfate and filtered through 200 ml of silica gel to yield 4.9 g of the title compound, melting point 265°-267° C.

後処理

  1. temperatureheated at 110° C for an additional 18 hours
  2. extractionextracted several times with dichloromethane
  3. dry with materialThe combined dichloromethane extracts are dried over sodium sulfate
  4. filtrationfiltered through 200 ml of silica gel

出典と根拠

ORDレコード
ord-7cec077cb34c443e804fe683efd50ce5
出典データセット
uspto-grants-1977_12
特許番号
US04061655

反応ノート

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