4-tert-Butylbenzonitrile → HCID 178440935, Verbindung

HRID 925018

Reaktionsgleichung

Reaktionsgleichung von HRID 925018
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[C:17]([C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>O>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[C:1]([CH3:4])([CH3:2])[CH3:3])=[NH:26])=[CH:27][CH:28]=1)([CH3:20])([CH3:18])[CH3:19]

Komponenten

5

Edukt 3

HCID 778834-tert-ButylbenzonitrileHCID 805742-tert-ButylanilineHCID 178418339Butyllithium

Produkt 1

HCID 178440935HCID 178440935, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Procedure as described for Amidine I using the following amounts: 7.80 mL of 2-t-butylaniline (50.0 mmol); 25.0 mL of 2.0 M butyllithium (50.0 mmol), 8.50 ml of 4-t-butylbenzonitrile (50.0 mmol). After refluxing overnight, the solution was dark brown. Addition of water yielded an orange solution with suspended solid. Solution was filtered and taken to dryness. The residue was treated with 75 mL of pentane, stirred for 30 minutes, and filtered yielding 13.43 g (87%) of light orange solid. 1H NMR (400 MHz, CDCl3): 7.87 (d, 2H), 7.49 (d, 2H), 7.41 (d, 1H), 7.17 (t, 1H), 7.00 (t, 1H), 6.81 (d, 1 H), 4.75 (s, 2H), 1.41 (s, 9H), 1.36 (s, 9H).

Aufarbeitung

  1. temperatureAfter refluxing overnight
  2. customyielded an orange solution
  3. filtrationSolution was filtered
  4. additionThe residue was treated with 75 mL of pentane
  5. filtrationfiltered
  6. customyielding 13.43 g (87%) of light orange solid

Quellen und Nachweise

ORD-Eintrag
ord-786f35efc25a4ec3bdef2f03e83e14d1
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283555B2

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