Aniline → 4-Nitro-3-phenylaminobenzonitrile

HRID 242800

Reaktionsgleichung

Reaktionsgleichung von HRID 242800
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].[C:13]1([NH2:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CS(C)=O>[N+:10]([C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[NH:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-:12])=[O:11]

Komponenten

4

Edukt 2

HCID 6115AnilineHCID 27833993-Fluoro-4-nitrobenzonitrile

Produkt 1

HCID 681579814-Nitro-3-phenylaminobenzonitrileAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A suspension of 3-fluoro-4-nitrobenzonitrile (1.66 g, 10.0 mmol) in DMSO (5 mL) was purged with a stream of argon prior to addition of phenylamine (1.82 mL, 20.0 mmol) and then the mixture was stirred at 120° C. for 1 h under an argon atmosphere. After cooling to RT, the reaction mixture was partitioned between EtOAc (75 mL) and an aqueous solution of KHSO4 (100 mL). The organic layer was then washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was triturated with diethyl ether affording 4-Nitro-3-phenylaminobenzonitrile as red crystals (2.35 g, 98%). 1H NMR (CDCl3, 400 MHz): δ 9.48 (1H, bs), 8.29 (1H, d, J=8.76 Hz), 7.53-7.40 (3H, m), 7.35 (1H, t, J=7.52 Hz), 7.29-7.22 (2H, m), 6.97 (1H, d, J=8.79 Hz).

Aufarbeitung

  1. customwas purged with a stream of argon
  2. temperatureAfter cooling to RT
  3. customthe reaction mixture was partitioned between EtOAc (75 mL)
  4. washThe organic layer was then washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9d8f1c53e2a64e629f2c33cfb962b937
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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