Water → 9-Benzyl-3,6-dicyanocarbazole

HRID 460876Notes

Reaction equation

HRID 460876 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 213948759-Benzyl-3,6-dicyanocarbazoleYield 79.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7cec077cb34c443e804fe683efd50ce5
Source dataset
uspto-grants-1977_12
Patent number
US04061655

Reaction notes

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