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

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]

Participants

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

customequipped with a magnetic stirring bar and a nitrogen inlet tube
customThe flask is purged of air with nitrogen
customthe redish brown crystals thereby precipitated
customisolated from the solution by filtration
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

Linked notes

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