Reaction #2275677

ord-dcaee025a52d4eec942964c83baccecf

Reaction equation

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
Yield 76.0%

Reactants

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

Reagents

None

Solvents

CC(Cl)Cl
dichloroethane

Conditions

Temperature
70°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe mixture is heated
  2. 2
    Temperatureat reflux for 4 hours
  3. 3
    workup.ADDITIONThe mixture is poured onto ice-cold water
  4. 4
    Extractionextraction
  5. 5
    Otherthe extract is dried
  6. 6
    Otherthe solvent is evaporated
  7. 7
    OtherThe beige precipitate obtained
  8. 8
    Otheris recrystallized from a mixture of isopropyl ether and ethanol (ratio 10:1)

Procedure

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.

Source

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