Hydroxyamine hydrochloride → HCID 53837996, compound

HRID 266498Notes

Reaction equation

HRID 266498 reaction equation
C([O-])(=O)C.[Na+].[CH:6]1([C:9](=[O:33])[C:10](=[CH:29]OCC)[C:11]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[C:15]([O:23][CH2:24][CH2:25][O:26][CH3:27])[C:14]=2[Br:28])=[O:12])[CH2:8][CH2:7]1.Cl.[NH2:35]O>C(O)C>[Br:28][C:14]1[C:15]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[C:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:17]=[CH:18][C:13]=1[C:11]([C:10]1[CH:29]=[N:35][O:33][C:9]=1[CH:6]1[CH2:8][CH2:7]1)=[O:12]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54220402HCID 54220402, compound

Product 1

HCID 53837996HCID 53837996, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium acetate (1.65 g) was added to a stirred mixture of 3-cyclopropyl-2-ethoxymethylene-1-[2-bromo-3-(2-methoxyethoxy)-4-methylsulphonylphenyl]propan-1,3-dione (8.5 g) and hydroxylamine hydrochloride (1.77 g) in ethanol. The mixture was stirred at room temperature overnight and then evaporated to dryness. The residue was dissolved in ethyl acetate and washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness. The residue was chromatographed on silica eluted with a mixture of ethyl acetate and cyclohexane (1:5) to give 4-[2-bromo-3-(2-methoxyethoxy) 4-methylsulphonylbenzoyl]-5-cyclopropylisoxazole (compound 181) as a yellow oil (3.3 g), NMR (CDCl3), 1.3(2H, m), 1.4(2H,m), 2.6(1H, m), 3.3(3H, s), 3.5(3H, s), 3.9(2H, m), 4.5(2H, m), 7.3(1H, d), 8.0(1H, s), 8.1(1H, d).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customThe residue was chromatographed on silica
  8. washeluted with a mixture of ethyl acetate and cyclohexane (1:5)

Sources & evidence

ORD record
ord-1c873a77f8c440fd84b6e3665f01b1c7
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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