Water → HCID 21394878, compound

HRID 460874Notes

Reaction equation

HRID 460874 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)[CH2:21][CH2:22][CH3:23].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)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 107751409H-carbazole-3,6-dicarbonitrile

Product 1

HCID 21394878HCID 21394878, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A slurry of sodium hydride (50% in oil, 480 mg) in 50 ml of anhydrous dimethylformamide is treated with 3,6-dicyanocarbazole (2.17 g) and heated at 110° C for two hours. The reaction mixture is then treated dropwise with butylbromide (1.37 g) and heated for about 16 hours at 110° C. The reaction mixture is poured into water and the resultant precipitate collected by filtration. The solid is dissolved in dichloromethane and filtered through 200 ml of silica gel to yield 2.22 g of the title compound, melting point 215°-217°C.

Workup

  1. temperatureheated for about 16 hours at 110° C
  2. filtrationthe resultant precipitate collected by filtration
  3. dissolutionThe solid is dissolved in dichloromethane
  4. filtrationfiltered through 200 ml of silica gel

Sources & evidence

ORD record
ord-f29ea4de65b9469c96d3d2dc85787796
Source dataset
uspto-grants-1977_12
Patent number
US04061655

Reaction notes

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