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

HRID 1940706
Notes
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Reaction equation

HRID 1940706 reaction equation
[CH3:1][N:2](S(C1C=CC=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].[C:23]([C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29]([O:35][CH2:36][CH3:37])[CH:28]=1)([CH3:26])([CH3:25])[CH3:24].[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1Cl>C(Cl)(Cl)Cl>[C:23]([C:27]1[CH:34]=[CH:33][C:30]([C:31]2[N:2]([CH3:1])[N:3]=[C:4]([C:5]3[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=3[Cl:12])[N:32]=2)=[C:29]([O:35][CH2:36][CH3:37])[CH:28]=1)([CH3:26])([CH3:24])[CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 214636124-(tert-Butyl)-2-ethoxybenzonitrileHCID 53760501N-methyl-N-phenylsulfonyl-2-chloro-6-fluorobenzohydrazonoyl chloride

Product 1

HCID 214636525-(4-t-butyl-2-ethoxyphenyl)-3-(2-chloro-6-fluorophenyl) 1-methyl-1H-1,2,4-triazoleYield 11.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N-methyl-N-(benzenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (1.60 g), 4-t-butyl-2-ethoxybenzonitrile (1.00 g), anhydrous aluminum chloride (0.60 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 (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 0.20 g of desired compound (melting point: 108.0°-111.0° 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-0b2fcfb64e614fea891a0e41f3159360
Source dataset
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05700824

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes