Hydroxyamine hydrochloride → 4-Cyclopropylcarbonyl-5-[5-(methylsulphenyl)pyrid-2-yl]isoxazole

HRID 21447Notes

Reaction equation

HRID 21447 reaction equation
C([O-])(=O)C.[Na+].Cl.NO.[CH:9]1([C:12](=[O:28])[C:13](=[CH:24][N:25](C)C)[C:14]([C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][N:17]=2)=[O:15])[CH2:11][CH2:10]1>C(O)C>[CH:9]1([C:12]([C:13]2[CH:24]=[N:25][O:15][C:14]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][N:17]=2)=[O:28])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 53741367HCID 53741367, compound

Product 1

HCID 199317704-Cyclopropylcarbonyl-5-[5-(methylsulphenyl)pyrid-2-yl]isoxazoleYield 14.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium acetate (1.1 g) was added to a solution of hydroxylamine hydrochloride (0.9 g) and 3-cyclopropyl-2-(N,N -dimethylaminomethylene)-1-[5-(methylsulphenyl)-pyrid-2-yl]propan-1,3-dione (3.24 g) in ethanol. The mixture was stirred for 1 hour then cooled and filtered. The solid was washed with cold ethanol and the filtrate was partially evaporated. Water was added and the mixture was stirred at 0° C. for 0.5 hours. It was extracted with dichoromethane washed with water, dried (Na2SO4) and filtered. The flitrate was evaporated to dryness and the residue was purified by chromatography eluted with mixture of ethyl acetate and hexane to give 4-cyclopropylcarbonyl-5-[5-(methylsulphenyl)pyrid-2-yl] isoxazole (compound 13, 0.41 g) as a white solid, m.p. 103°-104° C.

Workup

  1. temperaturethen cooled
  2. filtrationfiltered
  3. washThe solid was washed with cold ethanol
  4. customthe filtrate was partially evaporated
  5. additionWater was added
  6. stirringthe mixture was stirred at 0° C. for 0.5 hours
  7. extractionIt was extracted with dichoromethane
  8. washwashed with water
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customThe flitrate was evaporated to dryness
  12. customthe residue was purified by chromatography
  13. washeluted with mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-f00189e4f95a44ae871b620818372d23
Source dataset
uspto-grants-1995_06
Patent number
US05424276

Reaction notes

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