Hydroxyamine hydrochloride → HCID 22621084, compound

HRID 430425Notes

Reaction equation

HRID 430425 reaction equation
Cl.NO.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:22])[C:12](=[CH:18][N:19](C)C)[C:13]([CH:15]2[CH2:17][CH2:16]2)=[O:14])=[C:7]([N:23]([CH2:28][CH3:29])[S:24]([CH3:27])(=[O:26])=[O:25])[CH:6]=1>C(O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:12]2[CH:18]=[N:19][O:14][C:13]=2[CH:15]2[CH2:17][CH2:16]2)=[O:22])=[C:7]([N:23]([CH2:28][CH3:29])[S:24]([CH3:27])(=[O:26])=[O:25])[CH:6]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 53878572HCID 53878572, compound

Product 1

HCID 22621084HCID 22621084, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (0.76 g) was added to a mixture of 1-[4-chloro-2-(N-ethyl-N-methylsulphonylamino)phenyl]-3-cyclopropyl-2-dimethylaminomethylenepropan-1,3-dione (3.83 g) in ethanol. The mixture was stirred for 1 hour and evaporated to dryness. The residue was dissolved in dichloromethane and washed with water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography eluted with a mixture of cyclohexane, dichloromethane and ethyl acetate. The product was triturated with a mixture of ether and hexane and filtered to give 4-[4-chloro-2-(N-ethyl-N-methylsulphonylamino)benzoyl]-5-cyclopropylisoxazole (compound 4, 0.81 g) as a white solid, mp. 114-115.8° C.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography
  8. washeluted with a mixture of cyclohexane, dichloromethane and ethyl acetate
  9. customThe product was triturated with a mixture of ether and hexane
  10. filtrationfiltered

Sources & evidence

ORD record
ord-af4d31e10fa9493584b3a49730d299f1
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

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