Sulfuric Acid → MLS003170801

HRID 1448129Notes

Reaction equation

HRID 1448129 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[C:6]([CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=O)[O:5][N:4]=1)[CH3:2].S(=O)(=O)(O)O>>[CH2:1]([C:3]1[C:7]2[C:8](=[O:9])[N:10]([CH3:11])[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:12][C:6]=2[O:5][N:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 203821073-Ethyl-N-methyl-5-(2-oxo-2-phenylethyl)-1,2-oxazole-4-carboxamide

Product 1

HCID 332790MLS003170801

Procedure

A mixture of 11.0 g. (0.0405 mole) of 3-ethyl-N-methyl-5-phenacyl-4-isoxazole carboxamide and 120 ml. of 2 M sulfuric acid is refluxed for 18 hours. The mixture is cooled and extracted with methylene chloride. The methylene chloride layer is washed with water and then brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is triturated with ether and filtered to give 3-ethyl-5-methyl-6-phenyl-isoxazolo[4,5-c]pyridin-4(5H)-one, m.p. 167° to 169° C.

Workup

  1. additionA mixture of 11.0 g
  2. temperatureThe mixture is cooled
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride layer is washed with water
  5. dry with materialbrine, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue is triturated with ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-bba138568a264109b1e53d87c41f1c42
Source dataset
uspto-grants-1979_12
Patent number
US04179566

Reaction notes

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