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1,2-Dichlorobenzene → 3-(2-chlorophenyl)-5-(2-chloro-3-nitrophenyl) 1-methyl-1H-1,2,4-triazole

HRID 52204
Notes
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Reaction equation

HRID 52204 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].[Cl:22][C:23]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[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]=[CH:28][CH:29]=[C:30]([N+:31]([O-:33])=[O:32])[C:23]=2[Cl:22])[N:2]([CH3:1])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 217860112-Chloro-3-nitrobenzonitrileHCID 54508988N-methyl-N-phenylsulfonyl-2-chlorobenzohydrazonoyl chloride

Product 1

HCID 214635893-(2-chlorophenyl)-5-(2-chloro-3-nitrophenyl) 1-methyl-1H-1,2,4-triazoleYield 64%

Reagents, catalysts & solvents

1
HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N-methyl-N-(benzenesulfonyl)-2-chlorobenzohydrazonoyl chloride (1.72 g), 2-chloro-3-nitrobenzonitrile (1.00 g), anhydrous aluminum chloride (0.70 g) and o-dichlorobenzene (20 ml) is stirred at an oil bath temperature of 140° C. for 30 minutes. After cooling, the reaction mixture is dissolved in chloroform (100 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 1.12 g of desired compound (melting point: 124.0°-125.0° C.).

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-9683e4492fbb4a659468c8dee45d1603
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05616594

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes