Sodium Cyanide → (9-Ethyl-9H-carbazol-3-yl)ethene-1,1,2-tricarbonitrile

HRID 1860348Notes

Reaction equation

HRID 1860348 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH:16]=[C:17]([C:20]#[N:21])[C:18]#[N:19])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[C-:22]#[N:23].[Na+].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>CN(C)C=O.O.C(Cl)(Cl)Cl>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([C:22]#[N:23])=[C:17]([C:18]#[N:19])[C:20]#[N:21])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 290167[(9-Ethyl-9h-carbazol-3-yl)methylene]malononitrileHCID 178418268HCID 178418268, compound

Product 1

HCID 18627189(9-Ethyl-9H-carbazol-3-yl)ethene-1,1,2-tricarbonitrileYield 13.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

10.2 g (37.5 mmol) of N-ethyl-3-(2,2-dicyanoethenyl)carbazole and 100 ml of N,N-dimethylformamide as solvent were placed in a 500 ml four-necked flask with a mechanical stirrer and bulb-shaped cooler. To this was added an aqueous solution of 1.84 g (37.5 mmol) of sodium cyanide and 4.3 ml of water, which was stirred for 10 minutes. Further, 16.6 g of lead tetraacetate was added. The resultant product was subjected to the reaction for 30 minutes. After the reaction was completed, 200 ml of chloroform was added. To the resultant aqueous solution was added 100 ml of water. The resultant liquid was washed in a separatory funnel. To the washed liquid was added sodium sulfate, which was left to stand for 30 minutes and dehydrated. The dehydrated solution was concentrated in an evaporator and dried under vacuum to obtain a red solid, which was recrystallized in the presence of benzene to obtain 1.5 g of a red crystal.

Workup

  1. washThe resultant liquid was washed in a separatory funnel
  2. additionTo the washed liquid was added sodium sulfate, which
  3. waitwas left
  4. waitto stand for 30 minutes
  5. concentrationThe dehydrated solution was concentrated in an evaporator
  6. customdried under vacuum
  7. customto obtain a red solid, which
  8. customwas recrystallized in the presence of benzene

Sources & evidence

ORD record
ord-9191afe6f41748eaa827be4bc4d23ac3
Source dataset
uspto-grants-2003_03
Patent number
US06528657B2

Reaction notes

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