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

HRID 1736685Notes

Reaction equation

HRID 1736685 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:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])([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

Procedure

A mixture of 2,3-dichloronitrobenzene (92.5 g), tert-butylamine (138 ml) and ethanol (50 ml) is heated in a bomb at 150° for 3 days. Dilution with water, extraction with ethylacetate several times, drying with sodium sulfate, and concentration gives the title compound, IR (neat) 2970, 1532, 1484, 1447, 1366, 1348, 1192 and 755 cm-1 ; NMR (CDCl3) 7.73, 7.61, 7.07, 4.77 and 1.22 δ; MS (m/z) 172, 154, 142, 126, 114, 99 and 90.

Workup

  1. temperatureis heated in a bomb at 150° for 3 days
  2. extractionDilution with water, extraction with ethylacetate several times
  3. dry with materialdrying with sodium sulfate, and concentration

Sources & evidence

ORD record
ord-fcf291a2998a414f8d76fe04cf538737
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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