Diisopropylethylamine → Ethyl 4-(2-isopropyl-1H-imidazol-1-yl)-3-nitrobenzoate

HRID 72757

Reaktionsgleichung

Reaktionsgleichung von HRID 72757
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].[CH:16]([C:19]1[NH:20][CH:21]=[CH:22][N:23]=1)([CH3:18])[CH3:17].C(N(CC)C(C)C)(C)C>C(#N)C>[CH:16]([C:19]1[N:20]([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:21]=[CH:22][N:23]=1)([CH3:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Produkt 1

HCID 59198553Ethyl 4-(2-isopropyl-1H-imidazol-1-yl)-3-nitrobenzoateAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-fluoro-3-nitrobenzoate 4.26 g, 2-isopropylimidazole 2.20 g, N,N-diisopropylethylamine 5.2 mL and acetonitrile 40 mL was heated under reflux for 24 hours. After distilling the solvent off, water was added to the residue and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and removed of the solvent by distillation, to provide 4.95 g of the title compound.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. distillationAfter distilling the solvent off, water
  4. additionwas added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customremoved of the solvent by distillation

Quellen und Nachweise

ORD-Eintrag
ord-5ec2d21edca24238b918011c1f187676
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829000B2

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