Sodium hydride → HCID 10336689, compound

HRID 1198150Notes

Reaction equation

HRID 1198150 reaction equation
[C:1]1(/[C:7](=[N:14]/[OH:15])/[CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].Br[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O>[C:1]1(/[C:7](=[N:14]/[O:15][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])/[CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 5480613HCID 5480613, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10336689HCID 10336689, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 5 g (0.025 moles) of (Z)-1-phenyl-2-(imidazol-1-yl)ethanone oxime and 20 ml of dimethylformamide, 0.9 g (0.03 moles) of sodium hydride dispersion 80% are added portionwise at room temperature. Upon completion, stirring is continued till hydrogen evolution stops. Then 4.74 ml (0.03 moles) of ethyl 5-bromopentanoate are added dropwise at room temperature and stirring is continued for 6 hours. The reaction mixture is evaporated under vacuum, diluted with water and extracted with chloroform. The organic phase dried over CaCl2 is evaporated to dryness. The residue is purified by column chromatography over silica gel (eluant: chloroform/methanol=97/3). The pure fractions are collected and evaporated, yielding 4.41 g (53%) of ethyl (Z)-5-[1-phenyl-2-(imidazol-1-yl)ethylidene]aminoxypentanoate.

Workup

  1. additionare added portionwise at room temperature
  2. stirringstirring
  3. customThe reaction mixture is evaporated under vacuum
  4. additiondiluted with water
  5. extractionextracted with chloroform
  6. dry with materialThe organic phase dried over CaCl2
  7. customis evaporated to dryness
  8. customThe residue is purified by column chromatography over silica gel (eluant: chloroform/methanol=97/3)
  9. customThe pure fractions are collected
  10. customevaporated

Sources & evidence

ORD record
ord-53e3985729ed4976b780f23726ba8b0b
Source dataset
uspto-grants-1994_01
Patent number
US05280033

Reaction notes

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