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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 52229Generated: October 27, 2026

1,2-Dichlorobenzene → 5-[4-chloro-3-(5-trifluoromethylpyridine-2-yloxy)phenyl]-3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazole

https://huagongshe.com/reaction/52229

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichlorobenzeneHCID 7239—
Reactant4-Chloro-3-(5-trifluoromethylpyridine-2-yloxy)benzonitrileHCID 21463615—
ReactantN-methyl-N-(benzenesulfonyl)-2,6-difluorobenzohydrazonoyl chlorideHCID 53707170—
CatalystIron chloride (FeCl3)HCID 24380—
SolventChloroformHCID 6212—
Product5-[4-chloro-3-(5-trifluoromethylpyridine-2-yloxy)phenyl]-3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazoleHCID 2146360524.6%

Reaction Conditions

Temperature140 °C

Reaction Steps

A mixture of N-methyl-N-(benzenesulfonyl)-2,6-difluorobenzohydrazonoyl chloride (0.90 g), 4-chloro-3-(5-trifluoromethylpyridine-2-yloxy)benzonitrile (0.90 g), anhydrous iron (III) chloride (0.50 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 hexaneethyl acetate as eluent to give 0.30 g of desired compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05616594
Source datasetuspto-grants-1997_04
ORD IDord-77baf2e8159c40409244685c53cbc1a3
Source noteuspto-grants-1997_04