2-Oxime 2,3-butanedione → HCID 23076453, compound

HRID 2221581Notes

Reaction equation

HRID 2221581 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]=[O:13])[CH:7]=1)(=[O:4])=[O:3].[CH3:14][C:15](=[N:19]O)[C:16](=O)[CH3:17].[ClH:21].C(OCC)(=O)C>>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[O:13][C:16]([CH3:17])=[C:15]([CH2:14][Cl:21])[N:19]=2)[CH:7]=1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 63989692-Oxime 2,3-butanedioneHCID 13487153HCID 13487153, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 23076453HCID 23076453, compound

Procedure

A mixture of 3-formylphenyl methanesulfonate (41.40 g), 2,3-butanedione-2-oxime (20.91 g) and 4N hydrogenchloride-ethyl acetate solution (250 mL) was stirred at room temperature for 5 days. After concentration of the reaction mixture, the residue was decanted and washed with diethyl ether. To the obtained residue was added tetrahydrofuran (300 mL), and thionyl chloride (37.00 g) was further added. The mixture was heated under reflux for 3 hrs. The reaction mixture was concentrated and ethyl acetate was added to the residue. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography. 3-(4-Chloromethyl-5-methyl-1,3-oxazol-2-yl)phenyl methanesulfonate from the eluted portion of ethyl acetate-hexane (1:3 to 1:1, v/v) was obtained as colorless crystals (34.29 g, 55%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 102-103° C.

Workup

  1. customAfter concentration of the reaction mixture, the residue was decanted
  2. washwashed with diethyl ether
  3. additionTo the obtained residue was added tetrahydrofuran (300 mL), and thionyl chloride (37.00 g)
  4. additionwas further added
  5. temperatureThe mixture was heated
  6. temperatureunder reflux for 3 hrs
  7. concentrationThe reaction mixture was concentrated
  8. additionethyl acetate was added to the residue
  9. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-4d26c1c84091440f8f3925f5f591a547
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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