Acetic Acid → N-methyl-5-phenacyl-3-phenyl-4isoxazole carboxamide

HRID 867175Notes

Reaction equation

HRID 867175 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([CH2:16][CH:17]([OH:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C>[O-2].[O-2].[O-2].[Cr+6].O>[CH3:15][NH:14][C:12]([C:11]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8][O:9][C:10]=1[CH2:16][C:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:24])=[O:13]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 203050053-phenyl-5-(beta-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide

Product 1

HCID 20304991N-methyl-5-phenacyl-3-phenyl-4isoxazole carboxamide

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

A suspension of 50 g. (0.155 mole) of 3-phenyl-5-(β-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide and 800 ml. acetic acid at room temperature is treated dropwise rapidly with 18.4 g. (0.185 mole) of chromium trioxide in 185 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 2N sodium hydroxide, dried over anhydrous magnesium sulfate, fitered and evaporated in vacuo. The solid residue is triturated with hot ether, cooled to 0° C. and filtered to give N-methyl-5-phenacyl-3-phenyl-4-isoxazole carboxamide, m.p. 125° to 128° C.

Workup

  1. additionA suspension of 50 g
  2. customa portion of the acetic acid is removed in vacuo
  3. additionThe remainder is poured onto ice water
  4. extractionextracted with methylene chloride
  5. washThe methylene chloride layer is washed with 2N sodium hydroxide
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe solid residue is triturated with hot ether
  9. temperaturecooled to 0° C.
  10. filtrationfiltered

Sources & evidence

ORD record
ord-20d2170377584609a673dddcf56c0245
Source dataset
uspto-grants-1978_07
Patent number
US04103013

Reaction notes

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