Acetic Acid → 3-[1-(4-Aminobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

HRID 465839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465839
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([Cl:18])[N:11]=[C:10]2[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:6][CH:5]=1)([O-])=O.C(O)(=O)C>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([Cl:18])[N:11]=[C:10]2[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:23][CH:24]=1

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 665771703-[1-(4-Nitrobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

Produkt 1

HCID 665771723-[1-(4-Aminobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 0.2 g of 3-[1-(4-nitrobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol, 0.15 g of iron and 0.3 mL of glacial acetic acid in 10 mL of absolute ethanol was refluxed for 1 hour. The reaction mixture was concentrated to dryness and the residue was dissolved in 20 mL of water and the solution was made basic to pH 8 by adding K2CO3. The mixture was then extracted with ethyl acetate and the ethyl acetate layer was washed with water. The organic layer was concentrated to give a crude product which was purified by flash silica gel column chromatography (ethyl acetate elution). A pure product was obtained as an amorphous solid; NMR (200 MHz, CDCl3): δ6.76 and 6.62 (dd, 4H, J=8.5 Hz); 6.42-6.22 (m, 2H); 2.57 (t, 2H, J=7.3 Hz); 1.65 (m, 2H); 1.33 (m, 2H); 0.87 (t, 2H, J=7.3 Hz).

Aufarbeitung

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in 20 mL of water
  4. additionby adding K2CO3
  5. extractionThe mixture was then extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with water
  7. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7d51bd12b3dd493a80262a5b5c797312
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153197

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