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

HRID 1940728
Notes
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Reaction equation

HRID 1940728 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[F:12].[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][C:25]=1[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][N:34]=1.ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]2[N:2]([CH3:1])[N:3]=[C:4]([C:5]3[C:6]([F:12])=[CH:7][CH:8]=[CH:9][C:10]=3[F:11])[N:29]=2)=[CH:26][C:25]=1[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:40])([F:41])[F:42])=[CH:35][N:34]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 214636154-Chloro-3-(5-trifluoromethylpyridine-2-yloxy)benzonitrileHCID 53707170N-methyl-N-(benzenesulfonyl)-2,6-difluorobenzohydrazonoyl chloride

Product 1

HCID 214636055-[4-chloro-3-(5-trifluoromethylpyridine-2-yloxy)phenyl]-3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazoleYield 24.6%

Reagents, catalysts & solvents 2

HCID 24380
Iron chloride (FeCl3)
Catalyst
HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

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 hexane-ethyl acetate as eluent to give 0.30 g of desired compound.

Workup

  1. temperatureAfter cooling
  2. washwashed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline
  3. dry with materialThen, it is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate is purified by silica gel column chromatography
  6. additionusing mixed solvent of hexane-ethyl acetate as eluent

Sources & evidence

ORD record
ord-bcfb511835e045cb8dfcc2a9bfb46db9
Source dataset
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05700824

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes