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

HRID 1940731Notes

Reaction equation

HRID 1940731 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]([O:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][N:35]=2)[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]([O:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:36][N:35]=3)=[CH:32][C:25]=2[Cl:24])[N:2]([CH3:1])[N:3]=1

Participants

6

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 214636072-Chloro-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrileHCID 54347086N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride

Product 1

HCID 214636873-(2-chloro-6-fluorophenyl)-5-[2-chloro-4-(5-trifluoromethylpyridine-2-yloxy)phenyl]-1-methyl-1H-1,2,4-triazoleYield 53.1%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (2.25 g), 2-chloro-4-(5-trifluoromethylpyridine-2-yloxy)benzonitrile (1.88 g), anhydrous iron (III) chloride (1.07 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 (300 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 1.54 g of desired compound (melting point: 139.0°-141.0° C.).

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-83ee50683bf148488484636eb0d07e0d
Source dataset
uspto-grants-1997_12
Patent number
US05700824

Reaction notes

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