Azobisisobutyronitrile → HCID 12187011, compound

HRID 861995Notes

Reaction equation

HRID 861995 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][C:11]1[C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:14])([CH3:13])[CH3:1])=[N:7][C:8]([CH3:12])=[CH:9][CH:10]=1.[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

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 3251458N-(6-Methylpyridin-2-yl)pivalamide

Product 2

HCID 12187011HCID 12187011, compoundYield 47%HCID 14326706N-[6-(Bromomethyl)pyridin-2-yl]-2,2-dimethylpropanamideYield 33%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Carbontetrachloride (CCl4, 300 mL) and the product of Example 1 (50.6 g, 0.26 mol) were added to a 1 L flask equipped with a N2 inlet The solution was stirred until all solid dissolved. N-bromo-succinimide (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 6 h with a 500 watt reflector spot lamp. An additional 0.5 eq (23.4 g) of NBS was added to the reaction, and refluxing was continued for 2 h. After cooling the reaction to room temperature, it was filtered and all solvent was removed under reduced pressure. Flash chromatography (15/85 EtOAc/Hex) provided 31.6 g (47%) of title product and 22.2 g (33%) of the title material of Example 2.

Workup

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

Sources & evidence

ORD record
ord-a13d8f64444b4a6fa60c199ffb654212
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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