N-bromobutanimide → N-[6-(Bromomethyl)pyridin-2-yl]-2,2-dimethylpropanamide

HRID 656293Notes

Reaction equation

HRID 656293 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)=[O:4].[Br:15]N1C(=O)CCC1=O>CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:12][C:8]1[N:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:14])([CH3:13])[CH3:1])[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 3251458N-(6-Methylpyridin-2-yl)pivalamide

Product 1

HCID 14326706N-[6-(Bromomethyl)pyridin-2-yl]-2,2-dimethylpropanamideYield 5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2,2 ethyl-N-(6-methyl-2-pyridinyl)propaneamide (21-1) (32 g) and N-bromosuccinimide (29.6 g) were added to carbon tetrachloride (300 ml) and to the mixture was added AIBN (15 mg), followed by reluxing for 20 hours under light emitted by 500 W lamp. The resulting mixture was cooled to room temperature, filtered, and concentrated under reduced pressure. The residue was purified by column-chromatography (hexane/ethyl acetate=10/1) to yield the compound 21-2 (1.94 g, 5%) as a pure white solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column-chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-992db61ff61e4a0290ab8a231e1f7778
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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