Fumaronitrile → 3,6-Diheptylphthalonitrile

HRID 53295

Reaktionsgleichung

Reaktionsgleichung von HRID 53295
[CH2:1]([C:8]1S(=O)(=O)[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:22](#[N:27])/[CH:23]=[CH:24]/[C:25]#[N:26]>C(Cl)(Cl)Cl>[CH2:13]([C:10]1[CH:11]=[CH:12][C:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[C:24]([C:25]#[N:26])[C:23]=1[C:22]#[N:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Komponenten

4

Edukt 2

HCID 637930FumaronitrileHCID 147085092,5-Diheptylthiophene 1,1-dioxide

Produkt 1

HCID 147084983,6-DiheptylphthalonitrileAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In a typical experiment 2,5-diheptylthiophene 1,1-dioxide (2 g, 6.4×10-3 mole) and fumaronitrile (0.5 g, 6.4×10-3 mole) in chloroform (5 ml) were heated in a sealed tube to 180° for 18 H. The contents of the tube were evaporated to dryness and chromatographed over silica (toluene as eluent) to afford 3,6-diheptylphthalonitrile (0.98 g, 47%) as a yellow solid. The material was recrystallised from ethanol to afford a colourless solid, mp 44°-46° C. 1H-nmr (CDCl3) shows S 7.52 (s, 2H); 2.85 (t, 4H); 1.0-1.9 (m, 20H); 0.90 (t, 6H).

Aufarbeitung

  1. customThe contents of the tube were evaporated to dryness
  2. customchromatographed over silica (toluene as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-bf955285522748e793b2977ac1ebd74c
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618929

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