Reaktion #80483

Reaktionsgleichung

N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride

2-chloro-3-nitrobenzonitrile

aluminum chloride

o-dichlorobenzene

→

desired compound

Ausbeute 64.0%

3-(2-chloro-6-fluorophenyl)-5-(2-chloro-3-nitrophenyl) 1-methyl-1H-1,2,4-triazole

Ausbeute 64.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Waschenwashed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline in this order
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe concentrate is purified by silica gel column chromatography
6. 6
   workup.ADDITIONusing mixed solvent of hexaneethyl acetate as eluent

Vorschrift

A mixture of N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (1.90 g), 2-chloro-3-nitrobenzonitrile (1.19 g), anhydrous aluminum chloride (0.70 g) and o-dichlorobenzene (20 ml) is stirred at an oil bath temperature of 140° C. for 30 minutes. After cooling, the reaction mixture is dissolved in chloroform (100 ml), washed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline in this order, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography using mixed solvent of hexaneethyl acetate as eluent to give 1.19 g of desired compound (melting point: 112.0°-114.0° C.).

Quelle