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

HRID 1464853Notes

Reaction equation

HRID 1464853 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 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.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. additionThe reaction mixture is poured into ice-cold water
  3. extractionthe product is extracted with dichloromethane
  4. customdrying
  5. customthe solvent is evaporated off
  6. customThe beige precipitate obtained
  7. customis recrystallized from a mixture of isopropyl ether and ethanol (10:1 ratio)

Sources & evidence

ORD record
ord-a7c969b4b4194a2cb174f09fec56b422
Source dataset
uspto-grants-2015_04
Patent number
US08999299B2

Reaction notes

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