Triethylamine → 4-Nitro-N-(tert-octyl)benzamide

HRID 403091Notes

Reaction equation

HRID 403091 reaction equation
[C:1]([NH2:9])([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)([O-:19])=[O:18]>ClCCl>[N+:17]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:9][C:1]([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2])=[O:25])=[CH:27][CH:28]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 61017tert-Octylamine

Product 1

HCID 6980294-Nitro-N-(tert-octyl)benzamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Tert-octylamine (51.7 g, 0.4 mol) and triethylamine (61.2 ml, 0.44 mol) in 260 ml of dichloromethane were introduced into a reactor. It was heated to 70° C. then 4-nitrobenzoyl chloride (77.9 g, 0.42 mol) was added in small portions over 50 minutes. It was heated under reflux for 4 hours. The reaction mixture was poured over ice water; it was extracted with dichloromethane, dried and the solvent was evaporated off. The beige precipitate obtained was 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 were obtained in the form of an off-white powder and used as is in the next step.

Workup

  1. temperatureIt was heated
  2. temperatureunder reflux for 4 hours
  3. extractionit was extracted with dichloromethane
  4. customdried
  5. customthe solvent was evaporated off
  6. customThe beige precipitate obtained
  7. customwas recrystallized from a mixture of isopropyl ether and ethanol (ratio 10:1)
  8. customAfter drying under vacuum

Sources & evidence

ORD record
ord-f0eabef875d849798a1fa6e4fe0edf0f
Source dataset
uspto-grants-2014_06
Patent number
US08747816B2

Reaction notes

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