Tert-Butylamine → N-tert-Butyl-6-chloro-2-nitroaniline

HRID 558961Notes

Reaction equation

HRID 558961 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([NH2:16])([CH3:15])([CH3:14])[CH3:13]>C(O)C>[C:12]([NH:16][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][CH:5]=[CH:6][C:7]=1[Cl:8])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 185552,3-Dichloronitrobenzene

Product 1

HCID 10823273N-tert-Butyl-6-chloro-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2,3-dichloronitrobenzene (5 g, 26 mmol), tert-butylamine (7.4 ml, 71 mmol) and ethanol (2.5 ml) was heated at 150° C. in a sealed tube for 3 days. The mixture was evaporated, the residue taken up in EtOAc, washed with water and brine, dried and evaporated to afford a yellow oil; yield 5.3 g, 90%.

Workup

  1. customThe mixture was evaporated
  2. washwashed with water and brine
  3. customdried
  4. customevaporated
  5. customto afford a yellow oil

Sources & evidence

ORD record
ord-22442cb4135b498ca0fe8796808265fd
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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