Hydroxyamine hydrochloride → HCID 19931777, compound

HRID 21444Notes

Reaction equation

HRID 21444 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7]O.[CH:9]1([C:12](=[O:31])[C:13](=[CH:27]OCC)[C:14]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][C:17]=2[F:26])=[O:15])[CH2:11][CH2:10]1>C(O)C>[CH:9]1([C:12]([C:13]2[CH:27]=[N:7][O:15][C:14]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][C:17]=2[F:26])=[O:31])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54282814HCID 54282814, compound

Product 1

HCID 19931777HCID 19931777, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium acetate (7.4 g) was added to a mixture of hydroxylamine hydrochloride (6.3g) and 3-cyclopropyl-2-ethoxymethylene-1-(2-fluoro-4-methylsulphonylphenyl)-propan-1,3-dione (29.0g) in ethanol. The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water, dried (anhydrous magnesium sulphate) filtered and evaporated to dryness. The residue was triturated with ether and filtered. The resultant solid was recrystallized from methanol. The mother liquors from the recrystallization were combined and evaporated to dryness. The residue was purified by column chromatography on silica gel to give 4-cyclopropylcarbonyl-5-(2-fluoro-4-methylsulphonylphenyl)-isoxazole (compound 1) as a white solid, m.p. 129.5°-130.5° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was triturated with ether
  8. filtrationfiltered
  9. customThe resultant solid was recrystallized from methanol
  10. customThe mother liquors from the recrystallization
  11. customevaporated to dryness
  12. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0bf6a7dfdacb4fbdac4e47bc4f388eef
Source dataset
uspto-grants-1995_06
Patent number
US05424276

Reaction notes

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