4-Chlorobenzonitrile → HCID 178503254, Verbindung

HRID 901894

Reaktionsgleichung

Reaktionsgleichung von HRID 901894
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[CH3:14][S:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>>[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([C:10](=[NH:11])[NH:20][C:19]2[CH:21]=[CH:22][C:16]([S:15][CH3:14])=[CH:17][CH:18]=2)=[CH:8][CH:7]=1

Komponenten

4

Edukt 3

HCID 121634-ChlorobenzonitrileHCID 660384-(Methylthio)anilineHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 178503254HCID 178503254, VerbindungAusbeute 43,4 %

Reaktionsbedingungen

Temperatur
185 °C

Versuchsvorschrift

Finely powdered anhydrous aluminium chloride (0.83 g, 6 mmol) was added to a stirred mixture of 4-chlorobenzonitrile (0.6875 g, 5 mmol) and 4-methylthioaniline (0.695 g, 5 mmol) over a period of 30 min. The reaction mixture was heated at 180-190° C. for 3 hours with stirring and allowed to cool to 50° C. The resultant mixture was triturated with ethyl acetate and basified with sodium hydroxide (20%) solution. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulphate and concentrated to give the crude product, which was purified by column chromatography to yield the title compound (0.6 g, 43.4%, purity 98.8% by HPLC), mp 148-150° C. 1H-NMR (CDCl3):δ 2.48 (s, 3H), 6.90-6.97(m, 2H), 7.11-7.41(m, 4H), 7.74 (bs, 2H). MS m/z:277.0 (M+)

Aufarbeitung

  1. temperatureto cool to 50° C
  2. customThe resultant mixture was triturated with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b811785ca7544ad4885101366af2fe23
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365069B2

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