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

HRID 1908404Notes

Reaction equation

HRID 1908404 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-3025b53d33674cacbc0df451da09f42b
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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