Triethylamine → N-(4-iodophenyl)-2-nitroaniline

HRID 2107661Notes

Reaction equation

HRID 2107661 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[I:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(OCC)(=O)C>[I:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108934-IodoanilineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 15045509N-(4-iodophenyl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

According to the method of V. P. Chernetskii, A. I. Kiprianov, Zh. Obsch. Khim, 1956, 26, 3465, a mixture of 2-fluoronitrobenzene (14.0 g, 100 mmol), p-iodo aniline (10.95 g, 50 mmol) and triethylamine (13.9 ml, 100 mmol) was heated under reflux for 42 hours. The mixture was cooled, diluted with ethyl acetate (300 ml) washed consecutively with water (100 ml), 2N sodium hydroxide (100 ml) and brine (100 ml). The organic layer was dried (MgSO4), concentrated under reduced pressure and the residue was recrystallised from ethyl acetate to give N-(4-iodophenyl)-2-nitroaniline, 10.03 g, as bright orange needles, m.p. 171°-2° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 42 hours
  3. temperatureThe mixture was cooled
  4. washwashed consecutively with water (100 ml), 2N sodium hydroxide (100 ml) and brine (100 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-2daf728c78fc412b9763ad1a9535438d
Source dataset
uspto-grants-1990_06
Patent number
US04935430

Reaction notes

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