Sodium Cyanide → N-(4-methoxyphenyl)-3-(tricyanoethenyl)carbazole

HRID 1860351Notes

Reaction equation

HRID 1860351 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:21]3[CH:20]=[CH:19][C:18]([CH:22]=[C:23]([C:26]#[N:27])[C:24]#[N:25])=[CH:17][C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:5][CH:4]=1.[C-:28]#[N:29].[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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:21]3[CH:20]=[CH:19][C:18]([C:22]([C:28]#[N:29])=[C:23]([C:24]#[N:25])[C:26]#[N:27])=[CH:17][C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 18627171N-(4-methoxyphenyl)-3-(2,2-dicyanoethenyl)carbazoleHCID 178418268HCID 178418268, compound

Product 1

HCID 18627195N-(4-methoxyphenyl)-3-(tricyanoethenyl)carbazoleYield 27.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

1.00 g (2.87 mmol) of N-(4-methoxyphenyl)-3-(2,2-dicyanoethenyl)carbazole and 12.5 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 prepared from 0.15 g (2.87 mmol) of sodium cyanide and 0.5 ml of water, which was stirred for 10 minutes. Further, 1.74 g (3.93 mmol) of lead tetraacetate was added. The resultant product was subjected to the reaction for 30 minutes. After the reaction was completed, 100 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 0.30 g of a red crystal.

Workup

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

Sources & evidence

ORD record
ord-314515197ce14e4ba1e439436be62514
Source dataset
uspto-grants-2003_03
Patent number
US06528657B2

Reaction notes

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