Phosphorus oxychloride → 2-Chloro-6-(2-chlorophenyl)-5-(4-chlorophenyl)nicotinonitrile

HRID 13814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 13814
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:13][C:12](=O)[C:11]([C:15]#[N:16])=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:12]1[C:11]([C:15]#[N:16])=[CH:10][C:9]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:13]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychloride2×HCID 219849076-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 102371012-Chloro-6-(2-chlorophenyl)-5-(4-chlorophenyl)nicotinonitrile

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the product of Step B (1.5 g) was added POCl3 (5 mL). The reaction was heated to 100° C. for 17 hours. After cooling to room temperature the excess POCl3 was removed in vacuo before the residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3 solution. The solution was concentrated and purified via flash chromatography on silica gel eluted with 10% EtOAc in hexane affording the title compound. HPLC/MS: 358.9 (M+1), 360.9 (M+3); Rt=4.07 min.

Aufarbeitung

  1. customwas removed in vacuo before the residue
  2. dissolutionwas dissolved in EtOAc
  3. washwashed with saturated aqueous NaHCO3 solution
  4. concentrationThe solution was concentrated
  5. custompurified via flash chromatography on silica gel
  6. washeluted with 10% EtOAc in hexane affording the title compound

Quellen und Nachweise

ORD-Eintrag
ord-48d62cb6b197491f91d65aadea6106af
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728141B2

Notizen zur Reaktion

Wird geladen…