Azobisisobutyronitrile → HCID 67993023, compound

HRID 2203316Notes

Reaction equation

HRID 2203316 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:3]=1.C1C(=O)N([Br:20])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.BrC(C1OC=C(CBr)N=1)(C)C(OC)=O>C(Cl)(Cl)(Cl)Cl>[Br:20][C:7]([C:5]1[O:6][C:2]([CH3:1])=[CH:3][N:4]=1)([CH3:12])[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 67992953HCID 67992953, compoundHCID 77230840HCID 77230840, compound

Product 1

HCID 67993023HCID 67993023, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of the intermediate from Step B (0.322 g, 1.903 mmol), NBS (0.373 g, 2.09 mmol), and AIBN (0.016 g, 0.095 mmol) in 15 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 a 7:1 mixture of the indicated product and methyl 2-bromo-2-[4-(bromomethyl)-1,3-oxazol-2-yl]propanoate (pale yellow oil). The mixture was used in the next step without further purification.

Workup

  1. temperaturewas refluxed for 1 hour
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. customto give
  6. customThe mixture was used in the next step without further purification

Sources & evidence

ORD record
ord-9c304fd6eed14f4baf35a91c4aadb382
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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