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

HRID 52242

Reaction equation

HRID 52242 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-d09da8cf964749938e77b8540c98d8c7
Source dataset
uspto-grants-1997_04
Patent number
US05616594

Linked notes

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