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

HRID 2380194Notes

Reaction equation

HRID 2380194 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 dichloromethane washed with water, dried (Na2SO4) and filtered. The filtrate 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 dichloromethane
  8. washwashed with water
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customThe filtrate 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-0f3f4207d9fd4a08bf9dcdc7f61898ff
Source dataset
uspto-grants-1994_11
Patent number
US05366957

Reaction notes

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