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

HRID 72755

Reaktionsgleichung

Reaktionsgleichung von HRID 72755
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 591988521-(4-Chloro-2-nitrophenyl)-2-isopropyl-1H-imidazoleAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dc85e8bc09d24cedbfdd0e9b5eb4d8c7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829000B2

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