Sulfuric Acid → MLS003170801

HRID 2398270Notes

Reaction equation

HRID 2398270 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 2M 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]pyridin4(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-eb4b4f4a6e05460d93a0ce8fae8fff01
Source dataset
uspto-grants-1977_05
Patent number
US04024262

Reaction notes

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