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

HRID 1460295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1460295
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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4fdf781af39a4005817389f13721849f
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05070205

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