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

HRID 435557
Notes
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Reaction equation

HRID 435557 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].CN(C)C=O.[C:21]([C:23]([C:29]#[N:30])=[C:24](C#N)[C:25]#[N:26])#[N:22]>O>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:24]([C:25]#[N:26])=[C:23]([C:29]#[N:30])[C:21]#[N:22])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6836N-ethyl carbazoleHCID 12635Tetracyanoethylene

Product 1

HCID 18627189(9-Ethyl-9H-carbazol-3-yl)ethene-1,1,2-tricarbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

About 1 gram (5.24 × 10-3 3 moles) N-ethyl carbazole and 20 milliliters of dimethylformamide are placed in a 50 milliliter one neck flask equipped with a magnetic stirring bar and a nitrogen inlet tube. The flask is purged of air with nitrogen, the contents of the flask agitated and about 0.67 grams (5.24 × 10-3 moles) of tetracyanoethylene introduced into the flask. Upon the admixture of these materials the contents of the flask turns deep blue. This mixture is heated to 100° C for 20 hours, the contents of the flask poured into 60 milliliters of water at room temperature and the redish brown crystals thereby precipitated isolated from the solution by filtration and washed with ethanol. Yield: 1.13 grams brick red crystals m. p. 239°-241° C. Analysis: calculated, carbon 77, hydrogen 4.08, nitrogen 18.92; actual, carbon 77.24, hydrogen 4.07, nitrogen 18.78.

Workup

  1. customequipped with a magnetic stirring bar and a nitrogen inlet tube
  2. customThe flask is purged of air with nitrogen
  3. customthe redish brown crystals thereby precipitated
  4. customisolated from the solution by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-68f4db311fb54625a753fb7fe583c265
Source dataset
uspto-grants-1977_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04006017

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes