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Azobisisobutyronitrile → HCID 19385590, compound

HRID 2399458
Notes
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Reaction equation

HRID 2399458 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[C:8]#[N:9])=[CH:4][CH:3]=1.C1C(=O)N([Br:26])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[C:8]#[N:9])=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 193856812-(4-Methylphenoxy)-2-(2'-chlorophenyl)acetonitrile

Product 1

HCID 19385590HCID 19385590, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a CCl4 solution (5 mL) of the product (0.200 g) of Step B was added NBS (0.132 g, 0.95 eq) and a catalytic amount of AIBN. The reaction mixture was refluxed overnight. TLC indicated clean conversion to product, and the reaction mixture was cooled to room temperature and concentrated in vacuo. The crude product was purified on a silica gel flash chromatography column (120×30 mm) eluted with 5% ethyl acetate in hexane to afford 0.178 g (72%) of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified on a silica gel flash chromatography column (120×30 mm)
  4. washeluted with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-612756679a214ab591889113c1dd99fb
Source dataset
uspto-grants-1995_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05449682

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes