Tetracyanoethylene → 2-Cyano-3-(4-dibutylamino-2-methoxyphenyl)-2-butenedinitrile

HRID 85322

Reaktionsgleichung

Reaktionsgleichung von HRID 85322
[C:1]([C:3]([C:9]#[N:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])#N.[CH2:11]([N:15]([CH2:24][CH2:25][CH2:26][CH3:27])[C:16]1[CH:21]=[CH:20]C=[C:18]([O:22][CH3:23])[CH:17]=1)[CH2:12][CH2:13][CH3:14]>CN(C)C=O>[C:5]([C:4](=[C:3]([C:1]1[CH:20]=[CH:21][C:16]([N:15]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][C:18]=1[O:22][CH3:23])[C:9]#[N:10])[C:7]#[N:8])#[N:6]

Komponenten

4

Edukt 2

HCID 12635TetracyanoethyleneHCID 4068285N,N-Dibutyl-3-methoxybenzenamine

Produkt 1

HCID 861937742-Cyano-3-(4-dibutylamino-2-methoxyphenyl)-2-butenedinitrileAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

In 8 ml of N,N-dimethylformamide, 0.5 g (3.9 mmol) of tetracyanoethylene was dissolved. With stirring under ice cooling, 0.8 g (3.4 mmol) of dibutyl(3-methoxyphenyl)amine was dissolved in 2 ml of N,N-dimethylformamide and added dropwise. The mixture was stirred for 35 minutes. After the ice bath was removed, the mixture was further stirred for 2 hours. After the reaction mixture was poured into 100 ml of water, extraction with chloroform, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography and washed with hexane to give 0.88 g of a black crystal having a mp of 86° C. (yield: 77.2%).

Aufarbeitung

  1. additionadded dropwise
  2. stirringThe mixture was stirred for 35 minutes
  3. customAfter the ice bath was removed
  4. stirringthe mixture was further stirred for 2 hours
  5. additionAfter the reaction mixture was poured into 100 ml of water, extraction with chloroform
  6. washwashing with a saturated saline solution
  7. dry with materialdrying over anhydrous sodium sulfate, and concentration
  8. customThe residue was purified by silica gel column chromatography
  9. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-392e4ffe9a4b4b3cbb42e9ad5c532ef5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846955B2

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