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

HRID 2188495Notes

Reaction equation

HRID 2188495 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]>ClC(Cl)C>[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 63651,1-DichloroethaneSolvent

Conditions

Temperature
70 °C

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.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 4 hours
  3. additionThe mixture is poured onto ice-cold water
  4. extractionextraction
  5. customthe extract is dried
  6. customthe solvent is evaporated
  7. customThe beige precipitate obtained
  8. customis recrystallized from a mixture of isopropyl ether and ethanol (ratio 10:1)

Sources & evidence

ORD record
ord-dcaee025a52d4eec942964c83baccecf
Source dataset
uspto-grants-2012_12
Patent number
US08323624B2

Reaction notes

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