Azobisisobutyronitrile → HCID 19385620, compound

HRID 2399456Notes

Reaction equation

HRID 2399456 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[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]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19385683HCID 19385683, compound

Product 1

HCID 19385620HCID 19385620, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of the product of Step B (26 mg, 0.096 mmol) NBS (16 mg, 0.95 eq) and AIBN (2 mg, catalytic amount) in CCl4 (2 mL) was heated to reflux for 1 hour and then concentrated in vacuo. The residue was purified on a silica gel flash chromatography column (125×20 mm) eluted with 5% ethyl acetate/hexane to yield 21 mg (62%) of the title compound.

Workup

  1. temperatureto reflux for 1 hour
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified on a silica gel flash chromatography column (125×20 mm)
  4. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ce4be18d8d0e4d068c94bc7b84389c25
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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