Water → N-(1,1-Dimethylethyl)-4-nitrobenzenamine

HRID 1847719Notes

Reaction equation

HRID 1847719 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12].O>CS(C)=O>[C:11]([NH:15][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 9590p-Fluoronitrobenzene

Product 1

HCID 20095N-(1,1-Dimethylethyl)-4-nitrobenzenamineYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1-fluoro-4-nitro-benzene (1 g, 7.1 mmol) and tert-butylamine (1.5 g, 21 mmol) in DMSO (5 mL) was stirred at 75° C. overnight. The mixture was poured into water (10 mL) and extracted with EtOAc (7 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated under vacuum to dryness. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1) to afford N-tert-butyl-4-nitroaniline (1 g, 73%). 1H NMR (CDCl3, 400 MHz) δ 8.03-8.00 (m, 2H), 6.61-6.57 (m, 2H), 4.67 (brs, 1H), 1.42 (s, 9H).

Workup

  1. extractionextracted with EtOAc (7 mL×3)
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum to dryness
  5. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1)

Sources & evidence

ORD record
ord-fb5e69e441124c5e997f0de8279a3e48
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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