Benzoyl Peroxide → HCID 15480822, compound

HRID 1857358Notes

Reaction equation

HRID 1857358 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11](=[O:23])[N:12]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([CH3:16])=[CH:14][N:15]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[Br:1][CH2:16][C:13]1[N:12]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11](=[O:23])[C:10]([Cl:9])=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 15480821HCID 15480821, compound

Product 1

HCID 15480822HCID 15480822, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
75 °C

Procedure

N-BROMOSUCCINIMIDE (2.61 G, 14.7 MMOL) WAS ADDED TO A STIRRED SOLUTION OF 3-CHLORO-1-ETHOXYCARBONYLMETHYL-6-METHYLPYRAZINONE (3.38 G, 14.7 MMOL) IN DRY BENZENE (50 ML). BENZOYL PEROXIDE (70%, 30 MG, 0.087 MMOL) WAS ADDED AND THE SOLUTION WAS HEATED TO 75° C. AFTER 16 H THE MIXTURE WAS PARTITIONED BETWEEN METHYLENE CHLORIDE AND 5% SODIUM METABISULFITE. THE ORGANIC LAYER WAS DRIED (NA2SO4) AND EVAPORATED IN VACUO. THE RESIDUE WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (30% ETOAC/HEXANES) TO GIVE THE TITLE COMPOUND AS A CRYSTALLINE SOLID:

Workup

  1. customAFTER 16 H THE MIXTURE WAS PARTITIONED BETWEEN METHYLENE CHLORIDE AND 5% SODIUM METABISULFITE
  2. customTHE ORGANIC LAYER WAS DRIED (NA2SO4)
  3. customEVAPORATED IN VACUO
  4. customTHE RESIDUE WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (30% ETOAC/HEXANES)

Sources & evidence

ORD record
ord-42562b177f194f7f8f1243a1971cdcd7
Source dataset
uspto-grants-2000_11
Patent number
US06147078

Reaction notes

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