Reacción #80500

Ecuación de reacción

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

2-chloro-4-phenoxybenzonitrile

o-dichlorobenzene

→

desired compound

Rendimiento 4.1%

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

Rendimiento 4.1%

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Lavadowashed
3. 3
   workup.ADDITIONwith dilute hydrochrolic acid, dilute aqueous solution of sodium hydroxide and saline in this order
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe concentrate is purified by silica gel column chromatography
7. 7
   workup.ADDITIONusing mixed solvent of hexane-ethyl acetate as eluent

Procedimiento

A mixture of N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (3.30 g), 2-chloro-4-phenoxybenzonitrile (2.30 g), anhydrous iron (III) chloride (1.60 g) and o-dichlorobenzene (10 ml) is stirred at an oil bath temperature of 140° C. for 1 hour. After cooling, the reaction mixture is dissolved in chloroform (100 ml), washed with dilute hydrochrolic 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 hexane-ethyl acetate as eluent to give 0.15 g of desired compound (melting point: 135.0°-140.0° C.).

Fuente