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

HRID 861978Notes

Reaction equation

HRID 861978 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>N(C(C)(C)C#N)=NC(C)(C)C#N.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 37%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Carbon tetrachloride (CCl4, 300 mL) and the product from Example 1 (50.6 g, 0.26 mol) were placed in a 1-L flask equipped with a N2 inlet The solution was stirred until all solid dissolved. N-bromosuccinimide (NBS, 46.8 g, 0.26 mol) was then added to the reaction flask, followed by 2,2'-azobisisobutyronitrile (AIBN, 0.02 g). The reaction was heated to reflux for 7 h with a 500 watt reflector spot lamp. After cooling the reaction to room temperature, it was filtered and all solvent was removed under reduced pressure. Flash chromatography (15/85 ethyl acetate (EtOAc)/Hex) provided 24.89 g (37%) of title product.

Workup

  1. customequipped with a N2 inlet The solution
  2. dissolutiondissolved
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 7 h with a 500 watt reflector spot lamp
  5. temperatureAfter cooling
  6. customthe reaction to room temperature
  7. filtrationit was filtered
  8. customall solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-faf5c5d002fa4169b5db368af21777b5
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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