Hydrogen Peroxide → HCID 178436613, compound

HRID 2420869Notes

Reaction equation

HRID 2420869 reaction equation
[OH:1]O.[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[N:9][CH:10]=1)[CH3:4].O>CC(O)=O>[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[N+:9]([O-:1])[CH:10]=1)[CH3:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 59272530N-(5-ethylpyridin-2-yl)pivalamide

Product 1

HCID 178436613HCID 178436613, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

H2O2 (30%, 34 mL, 0.33 mol) was added to a solution of N-(5-ethylpyridin-2-yl)pivalamide (22 g, 0.11 mol) in HOAc (200 mL). The mixture was stirred overnight at 80° C. The reaction mixture was poured into water and was extracted with EtOAc. The organics were washed with sat. Na2SO3 and NaHCO3 before being dried over MgSO4. The solvent was evaporated in vacuo to afford 5-ethyl-2-pivalamidopyridine 1-oxide (16 g, 67%), which was used for the next step without further purification.

Workup

  1. extractionwas extracted with EtOAc
  2. washThe organics were washed with sat. Na2SO3 and NaHCO3
  3. dry with materialbefore being dried over MgSO4
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-eb72b52cd6784a958efe425797d001c3
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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