Tetracyanoethylene → 2-Cyano-3-[5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]-2-butenedinitrile

HRID 85323

Reaktionsgleichung

Reaktionsgleichung von HRID 85323
[C:1]([C:3]([C:9]#[N:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])#N.[CH2:11]([N:15]([CH2:31][CH2:32][CH2:33][CH3:34])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]2[S:25]C=[CH:27][CH:28]=2)=[C:18]([O:29][CH3:30])[CH:17]=1)[CH2:12][CH2:13][CH3:14]>CN(C)C=O>[C:5]([C:4](=[C:3]([C:1]1[S:25][C:24]([CH:23]=[CH:22][C:19]2[CH:20]=[CH:21][C:16]([N:15]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:17][C:18]=2[O:29][CH3:30])=[CH:28][CH:27]=1)[C:9]#[N:10])[C:7]#[N:8])#[N:6]

Komponenten

4

Edukt 2

HCID 12635TetracyanoethyleneHCID 68008836Dibutyl[3-methoxy-4-[2-(thiophene-2-yl)vinyl]phenyl]amine

Produkt 1

HCID 866676052-Cyano-3-[5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]-2-butenedinitrileAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In 7 ml of N,N-dimethylformamide, 235 mg (1.83 mmol) of tetracyanoethylene was dissolved. With stirring under ice cooling, 600 mg (1.75 mmol) of dibutyl[3-methoxy-4-[2-(thiophene-2-yl)vinyl]phenyl]amine was dissolved in 2 ml of N,N-dimethylformamide and added dropwise. The mixture was stirred for 1.5 hours. After the ice bath was removed, the mixture was stirred at room temperature for 1 hour and further stirred with heating at 50° C. overnight. After the reaction mixture was poured into 80 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 methanol to give 324 mg of a dark reddish crystal having a mp of 189-192° C. (yield: 41.8%).

Aufarbeitung

  1. additionadded dropwise
  2. stirringThe mixture was stirred for 1.5 hours
  3. customAfter the ice bath was removed
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. stirringfurther stirred
  6. additionAfter the reaction mixture was poured into 80 ml of water, extraction with chloroform
  7. washwashing with a saturated saline solution
  8. dry with materialdrying over anhydrous sodium sulfate, and concentration
  9. customThe residue was purified by silica gel column chromatography
  10. washwashed with methanol
  11. customto give 324 mg of a dark reddish crystal

Quellen und Nachweise

ORD-Eintrag
ord-a674ceb4ec954a34a54c2ac91ef6271e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846955B2

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