Hydroxyamine hydrochloride → Isoxachlortole

HRID 266500Notes

Reaction equation

HRID 266500 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 15452203Isoxachlortole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium acetate (1.93 g) was added to a mixture of 1-(4-chloro-2-methylsulphonylphenyl)-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-methylsulphonylbenzoyl)-5-cyclopropylisoxazole, compound 260 (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-1f82981d02d942068dbed5162d962df4
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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