Azobisisobutyronitrile → HCID 53978409, compound

HRID 2399450Notes

Reaction equation

HRID 2399450 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=2[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:4][CH:3]=1.C1C(=O)N([Br:28])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:28][CH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=2[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 54566991HCID 54566991, compound

Product 1

HCID 53978409HCID 53978409, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of the product of Step B (200 mg, 0.690 mmol), NBS (117 mg, 0.95 eq) and AIBN (10 mg, catalytic amount) in CCl4 (5 mL) was heated at reflux for 2 hours and then cooled and concentrated in vacuo. The residue was purified on a silica gel flash chromatography column (30×130 mm) eluted with 5% ethyl acetate/hexane to yield 128 mg (50%) of the title compound.

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on a silica gel flash chromatography column (30×130 mm)
  5. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7224d02a5df24ab39f41acaee60e89f6
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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