1-tert-butyl-2,4-dinitrobenzene → 4-(Tert-butyl)-3-nitroaniline

HRID 2109567Notes

Reaction equation

HRID 2109567 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1)([O-])=O.[S]>O>[C:10]([C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][C:6]=1[N+:14]([O-:16])=[O:15])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 2385901-tert-butyl-2,4-dinitrobenzeneHCID 5362487Sulfur

Product 1

HCID 3161634-(Tert-butyl)-3-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1,3-dinitro-4-tert-butylbenzene (10.0 g) in H2O (56 ml) was heated to reflux. A mixture of Na2S (21.42 g) and sulfur (2.85 g) in H2O (34 ml) was added over 1 h via an addition funnel. The reaction maintained at reflux for 1.5 h then cooled to RT and extracted with EtOAc. The organic extracts were combined and washed with H2O, brine, dried over MgSO4 and concentrated in vacuo to afford 4-tert-butyl-3-nitro-phenylamine which was used as is without further purification.

Workup

  1. temperaturewas heated to reflux
  2. additionwas added over 1 h via an addition funnel
  3. temperatureThe reaction maintained
  4. temperatureat reflux for 1.5 h
  5. extractionextracted with EtOAc
  6. washwashed with H2O, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bcadcf7ca3ff417db95a9a3bce5dd1b9
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

Loading…