5-Bromo-2-hydroxypyridine → 5-(Phenylthio)-2-pyridone

HRID 372733

Reaction equation

HRID 372733 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[S-:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[K+]>CN1CCCC1=O.O>[C:10]1([S:9][C:2]2[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 5995285-Bromo-2-hydroxypyridineHCID 11789364benzenethiol, potassium salt

Product 1

HCID 203265625-(Phenylthio)-2-pyridone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 5-bromo-2-pyridone (17.3 g 0.1 mole) in N-methylpyrrolidinone (250 ml.) and potassium thiophenoxide (18.1 g, 0.12 mole) is heated at reflux for 12 hours under a nitrogen atmosphere. The reaction mixture is cooled and diluted with water. The product is collected by filtration, washed with water and dried to yeild 5-(phenylthio)-2-pyridone.

Workup

  1. temperatureat reflux for 12 hours under a nitrogen atmosphere
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe product is collected by filtration
  4. washwashed with water
  5. dry with materialdried to yeild 5-(phenylthio)-2-pyridone

Sources & evidence

ORD record
ord-9ca0a3824ae444c9b4fee4d9894b9db9
Source dataset
uspto-grants-1978_05
Patent number
US04092321

Linked notes

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