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1,2-Dichlorobenzene → 3-(2-chlorophenyl)-1-methyl-5-[4-(6-methylhexyl)phenyl]-1H-1,2,4-triazole

HRID 1108946
Notes
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Reaction equation

HRID 1108946 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].[CH3:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1.[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:34]=[C:33]([C:32]2[CH:35]=[CH:36][C:29]([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22])=[CH:30][CH:31]=2)[N:2]([CH3:1])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 5758634-HeptylbenzonitrileHCID 6451240Aluminum(III) ChlorideHCID 54508988N-methyl-N-phenylsulfonyl-2-chlorobenzohydrazonoyl chloride

Product 1

HCID 190213703-(2-chlorophenyl)-1-methyl-5-[4-(6-methylhexyl)phenyl]-1H-1,2,4-triazoleYield 68.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2.06 g of N-methyl-N-phenylsulfonyl-2-chlorobenzohydrazonoyl chloride, 1.30 g of 4-(6-methylhexyl) benzonitrile, 0.93 g of anhydrous aluminum chloride and 5 ml of o-dichlorobenzene was stirred in an oil bath at a temperature of 140° C. for 30 minutes. After the cooling, the resulting solution was dissolved in 200 ml of chloroform, washed with diluted hydrochloric acid solution, diluted sodium hydroxide aqueous solution and saline water in this order, dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting concentrate was purified through a chromatography of silica gel column using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 1.52 g of the given compound (melting point: 64.0°-67.0° C.).

Workup

  1. washwashed with diluted hydrochloric acid solution, diluted sodium hydroxide aqueous solution and saline water in this order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. concentrationThe resulting concentrate
  5. customwas purified through a chromatography of silica gel column

Sources & evidence

ORD record
ord-22797ca54e3d48d7b448cc4eef35e9f1
Source dataset
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05318959

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes