Azobisisobutyronitrile → HCID 67996613, compound

HRID 2203309Notes

Reaction equation

HRID 2203309 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9].[Br:13]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:13][C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)([CH3:12])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 63968586methyl 2-(pyrazin-2-yl)propanoate

Product 1

HCID 67996613HCID 67996613, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A carbon tetrachloride (150 mL) solution containing the intermediate from Step B (18 g, 108 mmol), N-bromosuccinimide (26.6 g, 150 mmol) and AIBN (0.5 g) was heated at reflux overnight. The solution was cooled to room temperature, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. m/z=245.1 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. customto give the indicated product

Sources & evidence

ORD record
ord-531f5a0296e44b3f89ecdeabe25e1dcf
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

Loading…