Hydroxyamine hydrochloride → Isoxachlortole

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

Procedure

Sodium acetate (1.93 g) was added to a mixture of 1-(4-chloro-2-methylsulphonylphenyl)-3-cyclopropyl-2-ethoxymethylenepropan 1,3-dione (84 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.