Reaktion #80518

Reaktionsgleichung

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

3-methoxy-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrile

o-dichlorobenzene

→

desired compound

Ausbeute 58.5%

3-(2-chloro-6-fluorophenyl)-5-[3-methoxy-4-(5-trifluoromethylpyridine 2-yloxy)phenyl]-1-methyl-1H-1,2,4-triazole

Ausbeute 58.5%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Waschenwashed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline
3. 3
   TrocknenThen, it is dried 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 hexane-ethyl acetate as eluent
7. 7
   Waschenwashed with hexane

Vorschrift

A mixture of N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (3.75 g), 3-methoxy-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrile (3.03 g), anhydrous iron (III) chloride (1.70 g) and o-dichlorobenzene (5 ml) is stirred at an oil bath temperature of 140° C. for 30 minutes. After cooling, it is dissolved in chloroform (300 ml) and washed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline. Then, it is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography using mixed solvent of hexane-ethyl acetate as eluent and washed with hexane to give 2.80 g of desired compound.

Quelle