Water → 2-[5-[2-(2-Benzyloxy-4-dibutylaminophenyl)vinyl]thiophene-2-yl]-3-cyano-2-butenedinitrile

HRID 85320

Reaktionsgleichung

Reaktionsgleichung von HRID 85320
[C:1]([C:3]([C:9]#[N:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])#N.[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([N:32]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH:22]=[CH:23][C:24]=1[CH:25]=[CH:26][C:27]1[S:28]C=[CH:30][CH:31]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.C(Cl)(Cl)Cl>CN(C)C=O>[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([N:32]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH:22]=[CH:23][C:24]=1[CH:25]=[CH:26][C:27]1[S:28][C:1]([C:3](=[C:4]([C:7]#[N:8])[C:5]#[N:6])[C:9]#[N:10])=[CH:30][CH:31]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6212ChloroformHCID 12635TetracyanoethyleneHCID 68008929[3-Benzyloxy-4-[2-(thiophene-2-yl)vinyl]phenyl]dibutylamine

Produkt 1

HCID 866676042-[5-[2-(2-Benzyloxy-4-dibutylaminophenyl)vinyl]thiophene-2-yl]-3-cyano-2-butenedinitrileAusbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

In 3 ml of N,N-dimethylformamide, 0.13 g (1.01 mmol) of tetracyanoethylene was dissolved. With stirring under ice cooling, 0.4 g (0.95 mmol) of [3-benzyloxy-4-[2-(thiophene-2-yl)vinyl]phenyl]dibutyl amine was dissolved in 1 ml of N,N-dimethylformamide and added dropwise. The mixture was stirred for 40 minutes and further stirred with heating at 40° C. overnight. 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 ethanol to give 157 mg of a black crystal having a mp of 125-130° C. (yield: 31.7%).

Aufarbeitung

  1. additionadded dropwise
  2. stirringThe mixture was stirred for 40 minutes
  3. stirringfurther stirred
  4. washwashing with a saturated saline solution
  5. dry with materialdrying over anhydrous sodium sulfate, and concentration
  6. customThe residue was purified by silica gel column chromatography
  7. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-77753e04cf7442b29f50ed8998c89950
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846955B2

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