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

HRID 1940721Notes

Reaction equation

HRID 1940721 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][CH:37]=[CH:36][CH: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][CH:37]=[CH:36][CH:35]=3)=[CH:32][C:25]=2[Cl:24])[N:2]([CH3:1])[N:3]=1

Participants

6

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 115576702-Chloro-4-phenoxybenzonitrileHCID 54347086N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride

Product 1

HCID 214636213-(2-chloro-6-fluorophenyl)-5-(2-chloro-4-phenoxyphenyl) 1-methyl-1H-1,2,4-triazoleYield 4.1%

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 (3.30 g), 2-chloro-4-phenoxybenzonitrile (2.30 g), anhydrous iron (III) chloride (1.60 g) and o-dichlorobenzene (10 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 hydrochrolic 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 0.15 g of desired compound (melting point: 135.0°-140.0° C.).

Workup

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

Sources & evidence

ORD record
ord-2689dbe3f8804cf89d1519ef62c943db
Source dataset
uspto-grants-1997_12
Patent number
US05700824

Reaction notes

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