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 1418607ノート

反応式

HRID 1418607 の反応式
[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]

参加物

7

反応物 3

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

生成物 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-carbaldehyde収率 27.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

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'-bromomethylbiphenyl-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.

後処理

  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

出典と根拠

ORDレコード
ord-e6e98008972c4192ac9d267fcf55ee20
出典データセット
uspto-grants-1999_03
特許番号
US05883111

反応ノート

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