Pyridine → N-(5-chloro-2-cyanophenyl)benzamide

HRID 244219

Reaktionsgleichung

Reaktionsgleichung von HRID 244219
[NH2:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].N1C=CC=CC=1.[C:17]1([C:23](Cl)=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([NH:1][C:23](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 170059Benzonitrile, 2-amino-4-chloro-

Produkt 1

HCID 57681047N-(5-chloro-2-cyanophenyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-4-chlorobenzonitrile (7.25 g, 47.5 mmol), in anh. pyridine (38 mL, 475 mmol) and DCM (300 mL) cooled in an ice-H2O bath under Ar was added PhCOCl (5.8 mL, 50 mmol) dropwise. The reaction was allowed to slowly warm to rt within the cooling bath and then was stirred at rt overnight. The reaction mixture was washed (H2O, 2 M aq HCl (2×), H2O, brine), dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a white solid; MS (ES+): m/z 257.1 (100) [MH+]; HPLC: tR=3.27 min (OpenLynx, polar—5 min).

Aufarbeitung

  1. washThe reaction mixture was washed (H2O, 2 M aq HCl (2×), H2O, brine)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3e592a22838d40b88166f9caa1c6ed7e
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653268B2

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