3-Chloro-4-(3,4-dichlorobenzyl)benzonitrile → 5-[3-chloro-4-(3,4-dichlorobenzyl)phenyl]-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole

HRID 52218Notes

Reaction equation

[CH3:1][N:2](S(C1C=CC=CC=1)(=O)=O)[N:3]=[C:4](Cl)[C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12].[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=1)[C:27]#[N:28]>C(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[Cl:23][C:24]1[CH:25]=[C:26]([C:27]2[N:2]([CH3:1])[N:3]=[C:4]([C:5]3[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=3[Cl:12])[N:28]=2)[CH:29]=[CH:30][C:31]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of N-methyl-N-(benzenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (1.00 g), 3-chloro-4-(3,4-dichlorobenzyl)benzonitrile (0.93 g), anhydrous iron (III) chloride (0.50 g) and o-dichtorobenzene (5 ml) is stirred at an oil bath temperature of 140° C. for 1 hour. After cooling, the reaction mixture is dissolved in chloroform (300 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 hexaneethyl acetate as eluent to give 0.64 g of desired compound (melting point: 179.0°-185.0° C.).

Workup

temperatureAfter cooling
washwashed
additionwith dilute hydrochrolic acid, dilute aqueous solution of sodium hydroxide and saline in this order
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe concentrate is purified by silica gel column chromatography
additionusing mixed solvent of hexaneethyl acetate as eluent

Sources & evidence

ORD record: ord-81c35234dda44d53a6bd8b273a56cc05
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616594

Reaction notes

Loading…