Diisopropylethylamine → Ethyl 4-[2-(1-ethylpropyl)-1H-imidazol-1-yl]-3-nitrobenzoate

HRID 576846

Reaktionsgleichung

Reaktionsgleichung von HRID 576846
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH2:16]([CH:18]([C:21]1[NH:22][CH:23]=[CH:24][N:25]=1)[CH2:19][CH3:20])[CH3:17].C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:16]([CH:18]([C:21]1[N:22]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])[CH:23]=[CH:24][N:25]=1)[CH2:19][CH3:20])[CH3:17]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2411062-pentan-3-yl-1H-imidazoleHCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Produkt 1

HCID 59198861Ethyl 4-[2-(1-ethylpropyl)-1H-imidazol-1-yl]-3-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Ethyl 4-fluoro-3-nitrobenzoate 9.16 g, 2-(1-ethylpropyl)-1H-imidazole 5.94 g, N,N-diisopropylethylamine 11.2 mL and acetonitrile 86 mL were mixed and heated under reflux for 15 hours in nitrogen atmosphere. From the reaction liquid the solvent was distilled off, and the residue was dissolved in ethyl acetate and rendered weakly alkaline with saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated, washed with water and dried over magnesium sulfate. Distilling the solvent off, 13.16 g of the title compound was obtained.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 15 hours in nitrogen atmosphere
  3. customFrom the reaction liquid the solvent
  4. distillationwas distilled off
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. distillationDistilling the solvent off, 13.16 g of the title compound
  10. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-5a13dbdccf6e43c9930819ada81fb1c0
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040536B2

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