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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 52239Generated: October 28, 2026

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

https://huagongshe.com/reaction/52239

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichlorobenzeneHCID 7239—
ReactantHCID 21463661HCID 21463661—
ReactantN-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chlorideHCID 54347086—
CatalystIron chloride (FeCl3)HCID 24380—
SolventChloroformHCID 6212—
Product3-(2-chloro-6-fluorophenyl)-5-[3-(3-chloro-5-trifluoromethylpyridine-2-yloxy)-5-methoxyphenyl]-1-methyl-1H-1,2,4-triazoleHCID 2146359448.7%

Reaction Conditions

Temperature140 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05616594
Source datasetuspto-grants-1997_04
ORD IDord-4003f433d55243c29521e770e2ecc5d0
Source noteuspto-grants-1997_04