Acetic Acid → 3-benzoyl-4-methyl-1,2,4-oxadiazol-5(4H)-one

HRID 1528339Notes

Reaction equation

HRID 1528339 reaction equation
[CH2:1]([C:8]1[N:12]([CH3:13])[C:11](=[O:14])[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:17])C>[O-2].[Cr+6].[O-2].[O-2]>[C:1]([C:8]1[N:12]([CH3:13])[C:11](=[O:14])[O:10][N:9]=1)(=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 215353933-benzyl-4-methyl-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 894434633-benzoyl-4-methyl-1,2,4-oxadiazol-5(4H)-oneYield 88%

Reagents, catalysts & solvents 1

HCID 10219390chromium (VI) trioxideCatalyst

Procedure

To a solution of 3-benzyl-4-methyl-1,2,4-oxadiazol-5(4H)-one (3.87 g, 20.34 mmol, 1 eq.) in acetic acid (120 ml) was added chromium(VI) oxide (6.10 g, 61.04 mmol, 3 eq.) and stirring was allowed overnight. The reaction was quenched by addition of water and extracted with Et2O (3×50 ml). The organics were combined, washed with aq. sat. NaHCO3, dried over MgSO4 and concentrated to give 3-benzoyl-4-methyl-1,2,4-oxadiazol-5(4H)-one (3.85 g, 88% yield) as a white solid.

Workup

  1. customThe reaction was quenched by addition of water
  2. extractionextracted with Et2O (3×50 ml)
  3. washwashed with aq. sat. NaHCO3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1eb77a2151744baaa250b50fc0f79003
Source dataset
uspto-grants-2015_07
Patent number
US09090600B2

Reaction notes

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