Hydroxyamine hydrochloride → Isoxachlortole

HRID 2393016Notes

Reaction equation

HRID 2393016 reaction equation
C([O-])(=O)C.[Na+].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:24])[C:14](=[CH:20]OCC)[C:15]([CH:17]2[CH2:19][CH2:18]2)=[O:16])=[C:9]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:8]=1.Cl.[NH2:30]O>C(O)C>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:14]2[CH:20]=[N:30][O:16][C:15]=2[CH:17]2[CH2:19][CH2:18]2)=[O:24])=[C:9]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:8]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54487700HCID 54487700, compound

Product 1

HCID 15452203IsoxachlortoleYield 57.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium acetate (1.93 g) was added to a mixture of 1-[4-chloro-2-(methylsulphonyl)phenyl]-3-cyclopropyl-2-ethoxymethylenepropan-1,3-dione (8.4 g) and hydroxylamine hydrochloride (1.64 g) in ethanol with stirring. The mixture was stirred at room temperature overnight. It was evaporated and the residue was dissolved in ethyl acetate, washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was recrystallized from ether to give 4-[4-chloro-2-(methylsulphonyl)benzoyl]-5-cyclopropylisoxazole (4.4 g) as an off-white solid, m.p. 183°-185° C.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customIt was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-bde397c97dc24744a05afdebd79ec1cd
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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