Acetic Anhydride → 4-Isobutylthio-2-pyridone

HRID 1009181Notes

Reaction equation

HRID 1009181 reaction equation
[CH2:1]([S:5][C:6]1[CH:11]=[CH:10][N+:9]([O-])=[CH:8][CH:7]=1)[CH:2]([CH3:4])[CH3:3].C(OC(=O)C)(=[O:15])C.[OH-].[Na+]>CO>[CH2:1]([S:5][C:6]1[CH:11]=[CH:10][NH:9][C:8](=[O:15])[CH:7]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 673058694-(isobutylthio)pyridine-N-oxide

Product 1

HCID 140726754-Isobutylthio-2-pyridone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 500 mg of 4-(isobutylthio)pyridine-N-oxide, 5 ml of acetic anhydride was heated at reflux for 10 hours. The mixture was cooled, then added MeOH and 3N NaOH was added dropwise at pH 9˜11 and stirred. After 1 hour solution was evaporated and 3N HCl was added dropwise at pH6.5˜7.5, extracted with ethyl acetate and subjected to silica gel column chromatography (hexane/ethyl acetate) to obtain the compound (90 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 hours
  3. temperatureThe mixture was cooled
  4. customAfter 1 hour solution was evaporated
  5. addition3N HCl was added dropwise at pH6.5˜7.5
  6. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-edc5021f1c0a4bbe9659f34c7ae2f93d
Source dataset
uspto-grants-2011_07
Patent number
US07973060B2

Reaction notes

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