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

HRID 1870919노트

반응식

HRID 1870919 반응식
[CH2:1]([C:5]1[NH:6][C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[O:33][C:32](=[O:34])[N:31](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:30]=2)=[CH:19][CH:18]=1>CN(C)C=O.O.FC(F)(F)C(O)=O>[CH2:1]([C:5]1[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[O:33][C:32](=[O:34])[NH:31][N:30]=3)=[CH:19][CH:18]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 186931495-(4'-Bromomethylbipenyl-2-yl)-2,3-dihydro-3-triphenylmethyl-1,3,4-oxadiazol-2-oneHCID 178418251HCID 178418251, 화합물

생성물 1

HCID 186931102-Butyl-4-chloro-1-[[2'-(2,3-dihydro-2-oxo-1,3,4-oxadiazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carbaldehyde수율 27.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6422Trifluoroacetic acid용매

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.

후처리

  1. stirringThe reaction mixture was stirred for 1.5 hour at room temperatures, which
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel
  7. customThe crude product thus obtained
  8. stirringthe solution was stirred for 30 minutes at 60° C
  9. customTrifluoroacetic acid was evaporated under reduced pressure
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. washthe solution was washed with an aqueous solution of sodium hydrogencarbonate
  12. customdried
  13. customThe solvent was evaporated under reduced pressure
  14. customthe residue was purified by column chromatography on silica gel
  15. customCrude crystals thus obtained
  16. customwas recrystallized from ethylacetate-hexane

출처 및 근거

ORD 기록
ord-b9b50a834b7644509d49493355e4df59
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100252

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