Reaction #1552035

ord-a7c969b4b4194a2cb174f09fec56b422

Reaction equation

CC(C)(C)CC(C)(C)N
tert-Octylamine
CCN(CC)CC
triethylamine
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
triethylamine
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 refluxed for 4 hours
  2. 2
    workup.ADDITIONThe reaction mixture is poured into ice-cold water
  3. 3
    Extractionthe product is extracted with dichloromethane
  4. 4
    Otherdrying
  5. 5
    Otherthe solvent is evaporated off
  6. 6
    OtherThe beige precipitate obtained
  7. 7
    Otheris recrystallized from a mixture of isopropyl ether and ethanol (10:1 ratio)

Procedure

tert-Octylamine (51.7 g, 0.4 mol) and triethylamine (61.2 ml, 0.44 mol) in 260 ml of dichloroethane are introduced into 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 in 50 minutes. The mixture is refluxed for 4 hours. The reaction mixture is poured into ice-cold water; the product is extracted with dichloromethane, drying is carried out, and the solvent is evaporated off. The beige precipitate obtained is recrystallized from a mixture of isopropyl ether and ethanol (10:1 ratio). 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 it is in the following stage.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08999299B2uspto-grants-2015_04