Reaktion #5328

Reaktionsgleichung

5-(4'-bromomethylbipenyl-2-yl-)-2,3-dihydro-3-triphenylmethyl-1,3,4-oxadiazol-2-one

2-butyl-4-chloroimidazole-5-carbaldehyde

sodium hydride

→

title compound

Ausbeute 27.6%

2-Butyl-4-chloro-1-[[2'-(2,3-dihydro-2-oxo-1,3,4-oxadiazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carbaldehyde

Ausbeute 27.6%

Lösungsmittel

N,N-dimethylformamide

water

trifluoroacetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 1.5 hour at room temperatures, which
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe extract was washed with water
4. 4
   Sonstigedried
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   Sonstigethe residue was purified by column chromatography on silica gel
7. 7
   SonstigeThe crude product thus obtained
8. 8
   workup.STIRRINGthe solution was stirred for 30 minutes at 60° C
9. 9
   SonstigeTrifluoroacetic acid was evaporated under reduced pressure
10. 10
    workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
11. 11
    Waschenthe solution was washed with an aqueous solution of sodium hydrogencarbonate
12. 12
    Sonstigedried
13. 13
    SonstigeThe solvent was evaporated under reduced pressure
14. 14
    Sonstigethe residue was purified by column chromatography on silica gel
15. 15
    SonstigeCrude crystals thus obtained
16. 16
    Sonstigewas recrystallized from ethylacetate-hexane

Vorschrift

To an ice-cooling solution of 2-butyl-4-chloroimidazole-5-carbaldehyde (0.19 g) in N,N-dimethylformamide (1 ml) was added sodium hydride (60% in oil; 44 mg), and the mixture was stirred for 10 minutes. To the mixture was then added 5-(4'-bromomethylbipenyl-2-yl-)-2,3-dihydro-3-triphenylmethyl-1,3,4-oxadiazol-2-one (0.57 g). The reaction mixture was stirred for 1.5 hour at room temperatures, which was diluted with water and extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel. The crude product thus obtained was dissolved in trifluoroacetic acid (4 ml), and the solution was stirred for 30 minutes at 60° C. Trifluoroacetic acid was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with an aqueous solution of sodium hydrogencarbonate and dried. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel. Crude crystals thus obtained was recrystallized from ethylacetate-hexane to afford the title compound as colorless prisms (0.12 g, 27%), m.p.178°-179° C.

Quelle