Water → HCID 18977973, compound

HRID 2393041Notes

Reaction equation

HRID 2393041 reaction equation
[CH:1]1([C:4](=[O:21])[C:5](=[CH:17][N:18](C)C)[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([S:15][CH3:16])[CH:9]=2)=[O:7])[CH2:3][CH2:2]1.Cl.NO.O>C(O)C>[CH:1]1([C:4]2[O:21][N:18]=[CH:17][C:5]=2[C:6](=[O:7])[C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([S:15][CH3:16])[CH:9]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 53940560HCID 53940560, compound

Product 1

HCID 18977973HCID 18977973, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-cyclopropyl-2-(N,N-dimethylaminomethylene)-1-(4-methyl-3-methylsulphenylphenyl)propan-1,3-dione (10.6 g) and hydroxylamine hydrochloride (2.92 g) in ethanol was stirred at room temperature overnight. Water was added and the mixture was evaporated to remove the ethanol. It was extracted with ethyl acetate, washed with aqueous sodium chloride solution, dried (sodium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluted with a mixture of ether and cyclohexane to give 5-cyclopropyl-4-(4-methyl-3-methylsulphenylbenzoyl)isoxazole (2.77 g) as a white solid, m.p. 85.5°-86.1° C.

Workup

  1. customthe mixture was evaporated
  2. customto remove the ethanol
  3. extractionIt was extracted with ethyl acetate
  4. washwashed with aqueous sodium chloride solution
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluted with a mixture of ether and cyclohexane

Sources & evidence

ORD record
ord-9f459dc1660347a09cf4323e27e31ed2
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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