p-Tolunitrile → HCID 178425631, Verbindung

HRID 925016

Reaktionsgleichung

Reaktionsgleichung von HRID 925016
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=1[NH2:6])([CH3:3])[CH3:2].C([Li])CCC.[CH3:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1>O>[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=1[NH:6][C:22](=[NH:23])[C:21]1[CH:24]=[CH:25][C:18]([CH3:17])=[CH:19][CH:20]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 7724p-TolunitrileHCID 789206-Isopropyl-o-toluidineHCID 178418339Butyllithium

Produkt 1

HCID 178425631HCID 178425631, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Procedure as described for Amidine I using the following amounts: 7.80 mL of 2-isopropyl-6-methylaniline (50.0 mmol); 25.0 mL of 2.0 M butyllithium (50.0 mmol), 5.86 g of 4-methylbenzonitrile (50.0 mmol). After refluxing overnight, the solution was dark brown. Addition of water yielded an orange-brown solution with suspended solid. Solution was filtered and taken to dryness. The residue was treated with 100 mL of pentane stirred overnight and filtered yielding 10.98 g (83%) of beige material. 1H NMR (400 MHz, CDCl3): 7.82 (d, 2H), 7.26 (d, 2H), 7.15 (d, 1H), 7.05 (d, 1H), 6.98 (t, 1 H), 4.56 (s, 2H), 3.09 (septet, 1H), 2.42 (s, 3H), 2.15 (s, 3H), 1.21 (d, 3H), 1.16 (d, 3H).

Aufarbeitung

  1. temperatureAfter refluxing overnight
  2. customyielded an orange-brown solution
  3. filtrationSolution was filtered
  4. additionThe residue was treated with 100 mL of pentane
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-906c0246865348dcac5e3dce902f80a1
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283555B2

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