1,2-Dichlorobenzene → 3-(2-chloro-6-fluorophenyl)-5-(2-chloro-4-nitrophenyl) 1-methyl-1H-1,2,4-triazole

HRID 1940704

Reaction equation

[CH3:1][N:2](S(C1C=CC(C)=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:24][C:25]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:26]=1[C:27]#[N:28].ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[Cl:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([F:11])[C:5]=1[C:4]1[N:28]=[C:27]([C:26]2[CH:29]=[CH:30][C:31]([N+:33]([O-:35])=[O:34])=[CH:32][C:25]=2[Cl:24])[N:2]([CH3:1])[N:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (1.90 g), 2-chloro-4-nitrobenzonitrile (1.80 g), anhydrous iron (III) chloride (1.60 g) and o-dichlorobenzene (5 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 hydrochloric 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 2.20 g of desired compound (melting point: 144.0°-148.0° C.).

Workup

temperatureAfter cooling
washwashed with dilute hydrochloric 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 hexane-ethyl acetate as eluent

Sources & evidence

ORD record: ord-62bbcfb7390543f9a29af9bd02493337
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05700824

Linked notes

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