Aniline → 2-Chloro-6-nitro-N-phenylaniline

HRID 242834

Reaktionsgleichung

Reaktionsgleichung von HRID 242834
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1F.[C:12]1([NH2:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[NH:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 6115AnilineHCID 750161-Chloro-2-fluoro-3-nitrobenzene

Produkt 1

HCID 30158142-Chloro-6-nitro-N-phenylanilineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 1-chloro-2-fluoro-3-nitrobenzene (983 mg, 5.60 mmol) in DMSO (3 mL) was purged with a stream of nitrogen prior to addition of phenylamine (1.0 mL, 11.2 mmol) and then stirred in a sealed tube at 100° C. for 3 h. After cooling to RT, the reaction mixture was partitioned between EtOAc and water. The organic layer was then washed with a saturated solution of KHSO4 (×3), then with water, followed by brine, dried (Na2SO4) and concentrated in vacuo affording (2-Chloro-6-nitrophenyl)phenylamine as a dark orange oil (1.35 g, 97%). 1H NMR (CDCl3, 400 MHz): δ 8.15 (1H, s), 8.03 (1H, dd, J=8.40, 1.49 Hz), 7.63 (1H, d, J=7.90 Hz), 7.32-7.23 (2H, m), 7.08-6.99 (2H, m), 6.86 (2H, d, J=7.90 Hz).

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. washThe organic layer was then washed with a saturated solution of KHSO4 (×3)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b433d264c3d343d1bf85b201933141df
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

Verknüpfte Notizen

Wird geladen…