Hydrogen Peroxide → HCID 118021257, compound

HRID 1056608Notes

Reaction equation

HRID 1056608 reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10](=[O:14])[N:11]([CH3:13])[N:12]=1.OO.C(=O)([O-])[O-].[K+].[K+].[Cl:24]CCl>C(O)(=O)C>[Cl:24][C:3]1[C:2]([CH3:1])=[C:7]([C:8]2[O:9][C:10](=[O:14])[N:11]([CH3:13])[N:12]=2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 118021448HCID 118021448, compound

Product 1

HCID 118021257HCID 118021257, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Step-3: 3-Methyl-4-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyridine-1-oxide: To a stirred solution of step-2 intermediate (1.0 g, 5.23 mmol) in acetic acid (30 mL) was added hydrogen peroxide (0.321 mL, 10.46 mmol) drop-wise at RT and the reaction was heated to 80° C. and maintained for 12 h. The resulting mixture was cooled to RT and basified with solid potassium carbonate. The resulting slurry was diluted with dichloromethane (50 mL) and filtered. The filtrate was concentrated under vacuum to afford 800 mg (88%) of title compound as white solid. 1HNMR (400 MHz, DMSO-d6) δ 8.34 (s, 1H), 8.19 (d, J=5.0 Hz, 1H), 7.67 (d, J=5.0 Hz, 1H), 3.43 (s, 3H), 2.45 (s, 3H).

Workup

  1. temperaturemaintained for 12 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-d127dae162274f2c8385cd5756e49424
Source dataset
uspto-grants-2016_07
Patent number
US09399638B2

Reaction notes

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