Tetracyanoethylene → 4-(Pyrrolidino) tricyanovinylbenzene

HRID 439588

Reaktionsgleichung

[C:1]1([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([C:14]([C:20]#[N:21])=[C:15](C#N)[C:16]#[N:17])#[N:13]>CN(C)C=O>[N:7]1([C:1]2[CH:6]=[CH:5][C:4]([C:15]([C:16]#[N:17])=[C:14]([C:20]#[N:21])[C:12]#[N:13])=[CH:3][CH:2]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

4-(pyrrolidino) tricyanovinylbenzene was prepared by mixing 1-phenylpyrrolidine (1.0 g, 6.8 mmol) with tetracyanoethylene (0.9 g, 7 mmol) in 10 mL dimethylformamide at 0° C. The reaction mixture was stirred at room temperature for three hours and at 40° C. for another ten hours. The reaction mixture was quenched with 25 mL water and the dark red colored aqueous solution was extracted with 150 mL methylene chloride and washed several times with water (150 mL). The organic layer was then separated, dried over Na2SO4 and evaporated. The crude products were purified through a silica gel column. The column was eluted with a 1:1 ratio solution of methylene chloride and hexane to yield 1.7 g of the pure product 4 (90% yield).

Aufarbeitung

customThe reaction mixture was quenched with 25 mL water
extractionthe dark red colored aqueous solution was extracted with 150 mL methylene chloride
washwashed several times with water (150 mL)
customThe organic layer was then separated
dry with materialdried over Na2SO4
customevaporated
customThe crude products were purified through a silica gel column
washThe column was eluted with a 1:1 ratio solution of methylene chloride and hexane

Quellen und Nachweise

ORD-Eintrag: ord-40b90836aa7f4cd4a75babfddc104f60
Quelldatensatz: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05514799

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