Hydroxyamine hydrochloride → HCID 86753444, compound

HRID 849653Notes

Reaction equation

HRID 849653 reaction equation
Cl.[NH2:2]O.[CH:4]1([C:7](=[O:27])[C:8](=[CH:23]OCC)[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([F:22])([F:21])([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[O:10])[CH2:6][CH2:5]1.C([O-])(=O)C.[Na+]>C(O)C>[CH:4]1([C:7]2[O:27][N:2]=[CH:23][C:8]=2[C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([S:17]([F:22])([F:21])([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1.[CH3:6][CH2:5][CH2:4][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 85410153HCID 85410153, compound

Product 1

HCID 86753444HCID 86753444, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (0.42 g) was added to a stirred solution of 3-cyclopropyl-2-ethoxymethylene-1-(4-pentafluorosulphanyl-phenyl)-propan-1,3-dione (0.97 g) in ethanol. Anhydrous sodium acetate (0.49 g) was then added and stirring maintained for 1 hour. The solvent was evaporated and the residue distributed between dichloromethane and water. The organic phase was dried (magnesium sulphate) and evaporated, and the residual oil purified by chromatography eluting with ethyl acetate/hexane to give after trituration with hexane 5-cyclopropyl-4-(4-pentafluorosulphanyl-benzoyl)isoxazole (Compound 1) as a white solid, m.p.57-58° C. Further elution gave, after trituration with hexane, 4-cyclopropylcarbonyl-5-(4-pentafluorosulphanylphenyl)isoxazole (Compound 2) as a white solid, m.p.53-55° C.

Workup

  1. temperaturemaintained for 1 hour
  2. customThe solvent was evaporated
  3. dry with materialThe organic phase was dried (magnesium sulphate)
  4. customevaporated
  5. customthe residual oil purified by chromatography
  6. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-6efa3f95a05c4cd09e5c50acb68ff286
Source dataset
uspto-grants-2000_01
Patent number
US06013805

Reaction notes

Loading…