Acetic Acid → 3-Ethyl-N-methyl-5-(2-oxo-2-phenylethyl)-1,2-oxazole-4-carboxamide

HRID 1448128Notes

Reaction equation

HRID 1448128 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[C:6]([CH2:12][CH:13]([OH:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:5][N:4]=1)[CH3:2].C(O)(=O)C>[O-2].[O-2].[O-2].[Cr+6].O>[CH2:1]([C:3]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[C:6]([CH2:12][C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:20])[O:5][N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 203488383-Ethyl-5-(2-hydroxy-2-phenylethyl)-N-methyl-1,2-oxazole-4-carboxamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

A solution of 29.0 g. (0.105 mole) of 3-ethyl-5-(β-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide and 500 ml. acetic acid at room temperature is treated dropwise rapidly with 12.5 g. (0.125 mole) of chromium trioxide in 125 ml. water. The resulting solution is stirred for 2 hours at room temperature and a portion of the acetic acid is removed in vacuo. The remainder is poured onto ice water and extracted with methylene chloride. The methylene chloride layer is washed with 2 N sodium hydroxide, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The solid residue is triturated with ether and recrystallized from ethanol to give 3-ethyl-N-methyl-5-phenacyl-4-isoxazole carboxamide, m.p. 134° to 136° C.

Workup

  1. customa portion of the acetic acid is removed in vacuo
  2. additionThe remainder is poured onto ice water
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride layer is washed with 2 N sodium hydroxide
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe solid residue is triturated with ether
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-df820710575e48db8ca7fc6b01134ca0
Source dataset
uspto-grants-1979_12
Patent number
US04179566

Reaction notes

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