3-Chloro-p-toluonitrile → 3-(2-chloro-6-fluorophenyl)-5-(3-chloro-4-methylphenyl) 1-methyl-1H-1,2,4-triazole

HRID 1940742Notes

Reaction equation

HRID 1940742 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:26]=[C:27]([CH:30]=[CH:31][C:32]=1[CH3:33])[C:28]#[N:29].[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1Cl>[Cl:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([F:11])[C:5]=1[C:4]1[N:29]=[C:28]([C:27]2[CH:30]=[CH:31][C:32]([CH3:33])=[C:25]([Cl:24])[CH:26]=2)[N:2]([CH3:1])[N:3]=1

Participants

5

Reactant 3

HCID 888943-Chloro-p-toluonitrileHCID 6451240Aluminum(III) ChlorideHCID 54347086N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride

Product 1

HCID 214636473-(2-chloro-6-fluorophenyl)-5-(3-chloro-4-methylphenyl) 1-methyl-1H-1,2,4-triazoleYield 55.1%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (7.50 g), 3-chloro-4-methylbenzonitrile (3.33 g), anhydrous aluminum chloride (3.00 g) and o-dichlorobenzene (20 ml) is stirred at an oil bath temperature of 140° C. for 1 hour. After cooling, it is washed with 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 3.70 g of desired compound.

Workup

  1. temperatureAfter cooling
  2. washit is washed with 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-b95a583e01284fc79bc0777a87d6b7c8
Source dataset
uspto-grants-1997_12
Patent number
US05700824

Reaction notes

Loading…