4-Chloro-1-fluoro-2-nitrobenzene → 1-(4-Chloro-2-nitrophenyl)-2-isopropyl-1H-imidazole

HRID 72755

Reaction equation

HRID 72755 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH:12]([C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)([CH3:14])[CH3:13].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:16]2[CH:17]=[CH:18][N:19]=[C:15]2[CH:12]([CH3:14])[CH3:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 676604-Chloro-1-fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 1234571H-Imidazole, 2-(1-methylethyl)-

Product 1

HCID 591988521-(4-Chloro-2-nitrophenyl)-2-isopropyl-1H-imidazoleYield 64.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-1-fluoro-2-nitrobenzene 1.01 g, 2-isopropylimidazole 634 mg, N,N-diisopropylethylamine, 1.46 mL and acetonitrile 12 mL was heated under reflux for 15 hours. The solvent was distilled off and water was added to the residue which was then rendred acidic with diluted hydrochloric acid. After washing the same with diethyl ether, the aqueous layer was rendered alkaline with aqueous sodium hydroxide solution and extracted twice with chloroform. The organic layer was washed with water, dried over magnesium sulfate, and removed of the solvent by distillation to provide 0.98 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. distillationThe solvent was distilled off
  4. additionwater was added to the residue which
  5. washAfter washing the same with diethyl ether
  6. extractionextracted twice with chloroform
  7. washThe organic layer was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customremoved of the solvent by distillation

Sources & evidence

ORD record
ord-dc85e8bc09d24cedbfdd0e9b5eb4d8c7
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Linked notes

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