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 1870919Notes

Reaction equation

HRID 1870919 reaction equation
[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]

Participants

7

Reactant 3

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

Product 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-carbaldehydeYield 27.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b9b50a834b7644509d49493355e4df59
Source dataset
uspto-grants-2000_08
Patent number
US06100252

Reaction notes

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