Triethylamine → 2-Isopropyl-4-nitro-benzoic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl ester

HRID 1910796

Reaktionsgleichung

Reaktionsgleichung von HRID 1910796
Br[CH2:2][CH2:3][O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16].C(N(CC)CC)C.[CH:26]([C:29]1[NH:30][CH:31]=[CH:32][N:33]=1)([CH3:28])[CH3:27]>CN(C=O)C.O>[CH:26]([C:29]1[N:30]([CH2:2][CH2:3][O:4][C:5](=[O:18])[C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=2[CH:15]([CH3:17])[CH3:16])[CH:31]=[CH:32][N:33]=1)([CH3:28])[CH3:27]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 1234571H-Imidazole, 2-(1-methylethyl)-HCID 671063212-Isopropyl-4-nitro-benzoic acid 2-bromo-ethyl ester

Produkt 1

HCID 671069432-Isopropyl-4-nitro-benzoic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl esterAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Isopropyl-4-nitro-benzoic acid 2-bromo-ethyl ester (0.19 g, 0.6 mmol) was dissolved in DMF (5 mL), then triethylamine (0.5 mL, 3.6 mmol) and 2-isopropylimidazole (0.2 g, 1.8 mmol) were added. The mixture was heated at reflux for 15 h then allowed to cool, diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography on silica gel (60-120 mesh), eluting with ethyl acetate, to afford 2-isopropyl-4-nitro-benzoic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl ester (90 mg, 43%) as an oil.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 h
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography on silica gel (60-120 mesh)
  9. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-910ae62a44824098a08c9d1881ef5e13
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604029B2

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