N-Hydroxyacetamidine → 5-{[4-(Methanesulfonyl)phenyl]methyl}-3-methyl-1,2,4-oxadiazole

HRID 2187902Notes

Reaction equation

HRID 2187902 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:27](=[N:30]O)([NH2:29])[CH3:28]>CN(C=O)C>[CH3:28][C:27]1[N:30]=[C:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=2)[O:14][N:29]=1

Participants

5

Reactant 3

HCID 30926N-HydroxyacetamidineHCID 682631,1'-CarbonyldiimidazoleHCID 5723454-Mesylphenylacetic acid

Product 1

HCID 99212855-{[4-(Methanesulfonyl)phenyl]methyl}-3-methyl-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(methylsulfonyl)phenylacetic acid (15 g, 70 mmol) in DMF (300 mL) at r.t., was added carbonyldiimidazole (12.5 g, 77 mmol). After 0.5 h at r.t., acetamide oxime (5.7 g, 77 mmol) was added. After stirring the resulting mixture overnight at r.t., the mixture was heated to 120° C. for 6 h. After cooling to r.t., the mixture was quenched with H2O, and extracted with EtOAc. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (Hex:EtOAc, 1:1) yielded (3-Methyl-1,2,4-oxadiazol-5-yl) [4-(methylsulfonyl)phenyl]methane.

Workup

  1. temperaturethe mixture was heated to 120° C. for 6 h
  2. temperatureAfter cooling to r.t.
  3. customthe mixture was quenched with H2O
  4. extractionextracted with EtOAc
  5. washThe organic extracts were washed (H2O, brine)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (Hex:EtOAc, 1:1)

Sources & evidence

ORD record
ord-55247a372dda474da846723c76d62d55
Source dataset
uspto-grants-2002_06
Patent number
US06410563B1

Reaction notes

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