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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 85325Erstellt: 24. Oktober 2026

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

https://huagongshe.com/de/reaction/85325

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktWaterHCID 962—
EduktEthyl AcetateHCID 8857—
EduktTetracyanoquinodimethaneHCID 73697—
EduktDibutyl[3-methoxy-4-[2-(thiophene-2-yl)vinyl]phenyl]amineHCID 68008836—
LösungsmittelDimethylformamideHCID 6228—
Produkt2-[4-[Cyano-[5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]methylene]-2,5-cyclohexadienylidene]malonnitrileHCID 8854927214,5%

Reaktionsbedingungen

Temperatur50 °C

Reaktionsschritte

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%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08846955B2
Quelldatensatzuspto-grants-2014_09
ORD IDord-184ab29b59fb470db7e82cfde172825b
Quellennotizuspto-grants-2014_09