Benzoyl Peroxide → HCID 12272663, compound

HRID 79426Notes

Reaction equation

HRID 79426 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:27][N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[C:29]1=[O:35]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:34][C:30]1[C:29](=[O:35])[N:28]([CH3:27])[CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2854801,3-Dimethyl-2-pyridone

Product 1

HCID 12272663HCID 12272663, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (2.17 g, 12.2 mmol) and benzoic peroxyanhydride (0.295 g, 1.22 mmol) were added to a flask containing a solution of 1,3-dimethylpyridin-2(1H)-one (1.50 g, 12.2 mmol) in carbon tetrachloride (250 mL, degassed with flowing N2 for 5 minutes). The mixture was heated at reflux for 3 hours. The reaction mixture was cooled to ambient temperature, filtered through filter paper, and the filtrate was concentrated under vacuum. The residue was suspended in diethyl ether (20 mL), stirred for 15 minutes, and the liquid was decanted. The solids were rinsed with diethyl ether (3×5 mL), then dried under vacuum to give 3-(bromomethyl)-1-methylpyridin-2(1H)-one as a yellow solid (1.1 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. filtrationfiltered
  4. filtrationthrough filter paper
  5. concentrationthe filtrate was concentrated under vacuum
  6. customthe liquid was decanted
  7. washThe solids were rinsed with diethyl ether (3×5 mL)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-b735f70c674e412ba35bcd78b5db8bd6
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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