Azobisisobutyronitrile → HCID 67992976, compound

HRID 2203320Notes

Reaction equation

HRID 2203320 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[C:5]([CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])[N:6]=1.C1C(=O)N([Br:20])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:20][C:7]([C:5]1[N:6]=[C:2]([CH3:1])[O:3][CH:4]=1)([CH3:12])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 67996655HCID 67996655, compound

Product 1

HCID 67992976HCID 67992976, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of the intermediate from Step B (2.336 g, 13.81 mmol), NBS (2.458 g, 13.81 mmol), and AIBN (0.113 g, 0.690 mmol) in 50 mL of CCl4 was refluxed for 1 hour. The mixture 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 compound (yellow oil). 1H NMR (CDCl3, 500 MHz) δ 7.72 (1H, s), 3.89 (3H, s), 2.50 (3H, s), 2.29 (3H, s).

Workup

  1. temperaturewas refluxed for 1 hour
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. customto give the indicated compound (yellow oil)

Sources & evidence

ORD record
ord-56b4c2c39a4c4d0d8b437ea59bbe03d2
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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