Phosphorus pentachloride → HCID 19879854, Verbindung

HRID 1885746

Reaktionsgleichung

Reaktionsgleichung von HRID 1885746
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7][C:8](=O)[C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].P(Cl)(Cl)(Cl)(Cl)[Cl:20]>>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]=[C:8]([Cl:20])[C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17]

Komponenten

3

Edukt 2

HCID 24819Phosphorus pentachlorideHCID 19879857N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 19879854HCID 19879854, Verbindung

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamide (6.0 g, 0.0212 mol) and phosphorus pentachloride (8.9 g, 0.0427 mol) is heated to 100° C. for three hours, concentrated in vacuo to remove excess phosphorus pentachloride and triturated with methylene chloride to obtain a solution of N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetimidoyl chloride in methylene chloride. The methylene chloride solution is treated with 2-chloroacrylonitrile (2.5 mL, 0.0319 mol) and triethylamine (5.9 mL, 0.0422 mol), stirred overnight at room temperature, diluted with water and extracted with ethyl acetate. The combined organic extracts are washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a residue. Chromatography of the residue using silica gel and a 4:1 hexanes/ethyl acetate solution gives the title product as a yellow solid (0.65 g, mp 258°-260° C.).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customto remove excess phosphorus pentachloride
  3. customtriturated with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-ec2e87a51c684b29b4ee6b50f767e9b8
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05145986

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