Hydroxyamine hydrochloride → HCID 22621084, compound

HRID 2393000Notes

Reaction equation

HRID 2393000 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 (MgSO4) 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 (0.81 g) as a white solid, m.p. 114°-115.8° C.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  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-24704597523f40f689c9556d497edb12
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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