반응 #5328

반응 방정식

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

수율 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

수율 27.6%

용매

N,N-dimethylformamide

water

trifluoroacetic acid

반응 조건

후처리

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

실험 절차

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.

출처