Benzoyl Peroxide → HCID 68297737, compound

HRID 920093Notes

Reaction equation

HRID 920093 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH2:13][CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]=1[CH3:19])=[O:4].[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH2:13][CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]=1[CH2:19][Br:20])=[O:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68297223HCID 68297223, compound

Product 1

HCID 68297737HCID 68297737, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-bromo-1-(2-ethyl-butyl)-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester (5.72 g, 17.3 mmol), N-bromosuccinimide (3.39 g, 19.1 mmol), and benzoyl peroxide (0.42 g, 1.73 mmol) in CCl4 (170 mL) was refluxed for 16 h. The resulting suspension was filtered, and the filtrate was evaporated in vacuo. The residue was purified by silica gel chromatography (0-20% EtOAc/hexanes) to give 4.9 g of the title compound as a yellow viscous oil. MS: (+) m/z 432.10 (M+Na).

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationThe resulting suspension was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by silica gel chromatography (0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-042771571dd2444aaf686c36ad9bbdb7
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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