Hydroxyamine hydrochloride → HCID 11143212, compound

HRID 378805Notes

Reaction equation

HRID 378805 reaction equation
[CH:1]1([C:4](=[O:24])[C:5](=[C:19](SC)[S:20][CH3:21])[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:9]=2[Cl:18])=[O:7])[CH2:3][CH2:2]1.Cl.[NH2:26]O.C([O-])(=O)C.[Na+]>C(O)C>[CH:1]1([C:4]2[O:24][N:26]=[C:19]([S:20][CH3:21])[C:5]=2[C:6](=[O:7])[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:9]=2[Cl:18])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 11047768HCID 11047768, compound

Product 1

HCID 11143212HCID 11143212, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-cyclopropyl-2-(bis(methylthio)methylene)-1-(2-chloro-4-methylsulfonylphenyl)propan-1,3-dione (123 mg, 0.304 mmol) in ethanol (15 mL) was added hydroxylamine hydrochloride (23 mg, 0.334 mmol) and sodium acetate (25 mg, 0.304 mmol). The resulting mixture was stirred at r.t. overnight, then evaporated to dryness and the residue was taken up in ethyl acetate, washed with water, dried and evaporated to dryness. The crude product was purified by preparative Thin-layer chromatography to give 90 mg of crystalline 5-cyclopropyl-3-methylthio-4-(2-chloro-4-methylsulfonylbenzoyl)isoxazole, m.p. 141° C.

Workup

  1. customevaporated to dryness
  2. washwashed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe crude product was purified by preparative Thin-layer chromatography

Sources & evidence

ORD record
ord-df0de0d7b98c4333b43c872cfe31c699
Source dataset
uspto-grants-2001_10
Patent number
US06297198B1

Reaction notes

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