N-bromobutanimide → HCID 86686334, compound

HRID 1043901Notes

Reaction equation

HRID 1043901 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[C:3]([CH3:10])=[N:4][C:5]([CH2:9][Br:18])=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 251368433-Bromo-2,4,6-trimethylpyridine

Product 1

HCID 86686334HCID 86686334, compoundYield 36.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-bromo-2,4,6-trimethylpyridine (15.6 g), NBS (13.9 g) and benzoyl peroxide (567 mg) was heated under reflux in a carbon tetrachloride solvent (300 mL) for two hours. The reaction mixture was cooled to room temperature and then filtered, and the filtration residue was washed with carbon tetrachloride. The resulting filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%) to give the title compound (8.00 g).

Workup

  1. temperaturewas heated
  2. filtrationfiltered
  3. washthe filtration residue was washed with carbon tetrachloride
  4. concentrationThe resulting filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%)

Sources & evidence

ORD record
ord-0d04b3a30164440fa7b1204d257ae0cf
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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