Sodium Cyanide → HCID 69988140, compound

HRID 1860355Notes

Reaction equation

HRID 1860355 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:32]#[N:33])[C:24]4[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=4)=[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-:34]#[N:35].[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:34]#[N:35])=[C:23]([C:32]#[N:33])[C:24]4[CH:25]=[C:26]([F:31])[CH:27]=[C:28]([F:30])[CH:29]=4)=[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 69989017HCID 69989017, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 69988140HCID 69988140, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

0.50 g (1.15 mmol) of N-(4-methoxyphenyl)-3-(2-cyano-2-(3,5-difluorophenyl)ethenyl) carbazole and 5 ml of N,N-dimethylformamide as solvent were placed in a 200 ml four-necked flask with a mechanical stirrer and bulb-shaped cooler. To this was added an aqueous solution prepared from 0.06 g (1.15 mmol) of sodium cyanide and 0.5 ml of water, which was stirred for 10 minutes. Further, 0.51 g (1.15 mmol) of lead tetraacetate was added. The resultant product was subjected to the reaction for 30 minutes. After the reaction was completed, 20 ml of chloroform was added. To the resultant solution was added 20 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 vermilion solid. The vermilion solid was recrystallized in the presence of ethanol to obtain 0.10 g of a vermilion crystal. The yield of the synthesized orange crystal was 19%, and its melting point was 140-142° C. The IR chart is shown in FIG. 23.

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 vermilion solid
  9. customThe vermilion solid was recrystallized in the presence of ethanol
  10. customto obtain 0.10 g of a vermilion crystal

Sources & evidence

ORD record
ord-2d2d1223ad894424971505f2f563e7fc
Source dataset
uspto-grants-2003_03
Patent number
US06528657B2

Reaction notes

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