Sodium hydride → HCID 14820401, compound

HRID 1088737Notes

Reaction equation

HRID 1088737 reaction equation
[H-].[Na+].[H][H].BrCCCCC(OCC)=O.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17](/[C:21](=[N:27]\[O:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])/[C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)[CH:16]=1>CN(C)C=O>[N:15]1[CH:20]=[CH:19][CH:18]=[C:17](/[C:21](=[N:27]/[O:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])/[C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 14820400HCID 14820400, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14820401HCID 14820401, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 10.2 parts of (E+Z)-(3-pyridinyl) (3-thienyl)methanone, oxime and 67.5 parts of N,N-dimethylformamide were added portionwise 2.4 parts of a sodium hydride dispersion 50% at room temperature during a period of 15 minutes. Upon completion, stirring was continued till hydrogen evolution had ceased. 12.5 Parts of ethyl 5-bromopentanoate were added dropwise during a period of 10 minutes. Upon complete addition, stirring was continued for 18 hours at room temperature. After evaporation in vacuo, the residue was stirred in water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified twice by column chromatography over silica gel using a mixture of trichloromethane and ethyl acetate (90:10 by volume) as eluent. The first fraction was collected and the eluent was evaporated in vacuo, yielding 5.5. parts (33.0%) of ethyl (E)-5-[[[(3-pyridinyl) (3-thienyl)methylen]amino]oxy]pentanoate as a residue (compound 37). The second fraction was collected and the eluent was evaporated in vacuo, yielding 5 parts (30.0%) of ethyl (Z)-5-[[[(3-pyridinyl) (3-thienyl)methylen]amino]oxy]pentanoate as a residue (compound 38).

Workup

  1. additionUpon complete addition
  2. stirringstirring
  3. customAfter evaporation in vacuo
  4. stirringthe residue was stirred in water
  5. extractionthe product was extracted with trichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified twice by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and ethyl acetate (90:10 by volume) as eluent
  11. customThe first fraction was collected
  12. customthe eluent was evaporated in vacuo
  13. customyielding 5.5
  14. customThe second fraction was collected
  15. customthe eluent was evaporated in vacuo

Sources & evidence

ORD record
ord-2dcadfc4b23e4a24ad907ff4e90cfd79
Source dataset
uspto-grants-1990_10
Patent number
US04963573

Reaction notes

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