Reaction #80517

Reaction equation

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

3-(3-chloro-5-trifluoromethylpyridine-2-yloxy)-5-methoxybenzonitrile

o-dichlorobenzene

→

desired compound

Yield 48.7%

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

Yield 48.7%

Solvents

chloroform

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Washwashed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline
3. 3
   DryingThen, it is dried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherThe concentrate is purified by silica gel column chromatography
6. 6
   workup.ADDITIONusing mixed solvent of hexane-ethyl acetate as eluent

Procedure

A mixture of N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (0.90 g), 3-(3-chloro-5-trifluoromethylpyridine-2-yloxy)-5-methoxybenzonitrile (0.80 g), anhydrous iron (III) chloride (0.80 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 (100 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 to give 0.60 g of desired compound.

Source