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

HRID 13801

Reaktionsgleichung

Reaktionsgleichung von HRID 13801
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=O)[C:12]([C:16]#[N:17])=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.O=P(Cl)(Cl)[Cl:27]>>[Cl:27][C:13]1[C:12]([C:16]#[N:17])=[CH:11][C:10]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[N:14]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychloride2×HCID 219848256-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 101506772-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrile

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 6-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-nitrile (40.75g) was added POCl3 (20 mL). The reaction was heated to 100° C. for 13 hours. After cooling to room temperature the excess POCl3 was removed in vacuo before the residue was dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3 solution. The solution was concentrated and purified via flash chromatography on silica gel with a gradient elution of 30% to 100% CH2Cl2 in hexane affording the title compound. HPLC/MS: 392.9 (M+1), 394.9 (M+3); Rt=4.45 min.

Aufarbeitung

  1. customwas removed in vacuo before the residue
  2. dissolutionwas dissolved in CH2Cl2
  3. washwashed with saturated aqueous NaHCO3 solution
  4. concentrationThe solution was concentrated
  5. custompurified via flash chromatography on silica gel with a gradient elution of 30% to 100% CH2Cl2 in hexane affording the title compound

Quellen und Nachweise

ORD-Eintrag
ord-f6e58b0c76784b2495f47166236c83c3
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728141B2

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