Triethylamine → HCID 15452204, compound

HRID 2393034Notes

Reaction equation

HRID 2393034 reaction equation
C([N:3](CC)CC)C.[Cl:8][C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:19](=[O:30])[C:20](=[CH:26]OCC)[C:21]([CH:23]1[CH2:25][CH2:24]1)=[O:22].Cl.NO>C(#N)C>[Cl:8][C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:19]([C:20]1[CH:26]=[N:3][O:22][C:21]=1[CH:23]1[CH2:25][CH2:24]1)=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 54282014HCID 54282014, compound

Product 1

HCID 15452204HCID 15452204, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (0.9 g) was added to a mixture of 1-[2-chloro-4-(methylsulphonyl)phenyl]-3-cyclopropyl-2-ethoxymethylenepropan-1,3-dione (3.5 g) and hydroxylamine hydrochloride (1.0 g) in acetonitrile and the mixture was stirred at room temperature for 1 hour and left to stand overnight. The mixture was evaporated to dryness and the residue was partitioned between ethyl acetate and water. The organic layer was dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography on silica eluted with ethyl acetate and toluene. The product was recrystallized from ethyl acetate and cyclohexane to give 4-[2-chloro-4-(methylsulphonyl)benzoyl]-5-cyclopropylisoxazole (0.98 g) as a white solid, m.p. 116° C.

Workup

  1. waitleft
  2. waitto stand overnight
  3. customThe mixture was evaporated to dryness
  4. customthe residue was partitioned between ethyl acetate and water
  5. dry with materialThe organic layer was dried (magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by column chromatography on silica
  9. washeluted with ethyl acetate and toluene
  10. customThe product was recrystallized from ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-c65c51b8e47948a5a47e694e31cd6a8e
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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