Water → 2-[4-[Cyano-[5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]methylene]-2,5-cyclohexadienylidene]malonnitrile

HRID 85325

Reaktionsgleichung

Reaktionsgleichung von HRID 85325
[CH:1]1[C:11](=[C:12]([C:15]#[N:16])[C:13]#[N:14])[CH:10]=[CH:9][C:3](=[C:4]([C:7]#[N:8])[C:5]#N)[CH:2]=1.[CH2:17]([N:21]([CH2:37][CH2:38][CH2:39][CH3:40])[C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[CH:29][C:30]2[S:31]C=[CH:33][CH:34]=2)=[C:24]([O:35][CH3:36])[CH:23]=1)[CH2:18][CH2:19][CH3:20].O.C(OCC)(=O)C>CN(C)C=O>[C:7]([C:4]([C:5]1[S:31][C:30]([CH:29]=[CH:28][C:25]2[CH:26]=[CH:27][C:22]([N:21]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:23][C:24]=2[O:35][CH3:36])=[CH:34][CH:33]=1)=[C:3]1[CH:2]=[CH:1][C:11](=[C:12]([C:15]#[N:16])[C:13]#[N:14])[CH:10]=[CH:9]1)#[N:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 73697TetracyanoquinodimethaneHCID 68008836Dibutyl[3-methoxy-4-[2-(thiophene-2-yl)vinyl]phenyl]amine

Produkt 1

HCID 885492722-[4-[Cyano-[5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]methylene]-2,5-cyclohexadienylidene]malonnitrileAusbeute 14,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In 8 ml of N,N-dimethylformamide, 375 mg (1.84 mmol) of 7,7,8,8-tetracyanoquinodimethane 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 hour and further stirred with heating at 50° C. overnight. After the reaction mixture was poured into 80 ml of water, extraction with ethyl acetate, 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 chloroform to give 132 mg of a yellowish white crystal having a mp of 211-214° C. (yield: 14.5%).

Aufarbeitung

  1. additionadded dropwise
  2. stirringThe mixture was stirred for 1 hour
  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 chloroform

Quellen und Nachweise

ORD-Eintrag
ord-184ab29b59fb470db7e82cfde172825b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846955B2

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