1,2-Dichlorobenzene → 3-(2-chlorophenyl)-5-(2-fluoro-5-hexylphenyl) 1-methyl-1H-1,2,4-triazole

HRID 52209Notes

Reaction equation

HRID 52209 reaction equation
[CH3:1][N:2](S(C1C=CC=CC=1)(=O)=O)[N:3]=[C:4](Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].[F:22][C:23]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:27][C:24]=1[C:25]#[N:26].[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl>[Cl:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]1[N:26]=[C:25]([C:24]2[CH:27]=[C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:29]=[CH:30][C:23]=2[F:22])[N:2]([CH3:1])[N:3]=1

Participants

6

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 214636622-Fluoro-5-hexylbenzonitrileHCID 54508988N-methyl-N-phenylsulfonyl-2-chlorobenzohydrazonoyl chloride

Product 1

HCID 214636793-(2-chlorophenyl)-5-(2-fluoro-5-hexylphenyl) 1-methyl-1H-1,2,4-triazoleYield 71.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N-methyl-N-(benzenesulfonyl)-2-chlorobenzohydrazonoyl chloride (2.06 g), 2-fluoro-5-hexylbenzonitrile (1.23 g), anhydrous aluminum chloride (0.88 g) and o-dichlorobenzene (5 ml) is stirred at an oil bath temperature of 140° C. for 30 minutes. After cooling, the reaction mixture is dissolved in chloroform (200 ml), washed with dilute hydrochloric 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 1.60 g of desired compound (refractive index: 1.5779).

Workup

  1. temperatureAfter cooling
  2. washwashed with dilute hydrochloric acid, dilute aqueous solution of sodium hydroxide and saline in this order
  3. dry with materialdried 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-3c395eff27954893972c7a0a34882edb
Source dataset
uspto-grants-1997_04
Patent number
US05616594

Reaction notes

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