Reaktion #2275677

ord-dcaee025a52d4eec942964c83baccecf

Reaktionsgleichung

CC(C)(C)CC(C)(C)N
tert-Octylamine
CCN(CC)CC
triethyamine
O=C(Cl)c1ccc([N+](=O)[O-])cc1
4-nitrobenzoyl chloride
→
CC(C)(C)CC(C)(C)NC(=O)c1ccc([N+](=O)[O-])cc1
4-nitro-N-(tert-octyl)benzamide
Ausbeute 76.0%

Edukte

CC(C)(C)CC(C)(C)N
tert-Octylamine
CCN(CC)CC
triethyamine
O=C(Cl)c1ccc([N+](=O)[O-])cc1
4-nitrobenzoyl chloride

Reagenzien

Keine

Lösungsmittel

CC(Cl)Cl
dichloroethane

Reaktionsbedingungen

Temperatur
70°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture is heated
  2. 2
    Temperaturat reflux for 4 hours
  3. 3
    workup.ADDITIONThe mixture is poured onto ice-cold water
  4. 4
    Extraktionextraction
  5. 5
    Sonstigethe extract is dried
  6. 6
    Sonstigethe solvent is evaporated
  7. 7
    SonstigeThe beige precipitate obtained
  8. 8
    Sonstigeis recrystallized from a mixture of isopropyl ether and ethanol (ratio 10:1)

Vorschrift

tert-Octylamine (51.7 g, 0.4 mol) and triethyamine (61.2 ml, 0.44 mol) are introduced into 260 ml of dichloroethane in a reactor. The mixture is heated to 70° C. and then 4-nitrobenzoyl chloride (77.9 g, 0.42 mol) is added in small portions over 50 minutes. The mixture is heated at reflux for 4 hours. The mixture is poured onto ice-cold water; extraction is carried out with dichloromethane, the extract is dried and the solvent is evaporated. The beige precipitate obtained is recrystallized from a mixture of isopropyl ether and ethanol (ratio 10:1). After drying under vacuum, 84.6 g (Yield 76%) of 4-nitro-N-(tert-octyl)benzamide are obtained in the form of an off-white powder which is used as is in the following stage.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08323624B2uspto-grants-2012_12