Azobisisobutyronitrile → HCID 23365403, compound

HRID 1080725Notes

Reaction equation

HRID 1080725 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1.CC(N=NC(C#N)(C)C)(C#N)C.[Br:31]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 23365443HCID 23365443, compound

Product 1

HCID 23365403HCID 23365403, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 123 mg (0.492 mmol) of 4-methyl-2'-(2-thienyl)-1,1'-biphenyl, 18.5 mg of AIBN and 110 mg (0.62 mmol) of N-bromosuccinimide in 50 mL of carbon tetrachloride was heated at reflux until a negative starch iodide reaction was obtained (2 hr). The reaction mixture was evaporated under vacuum and the residue triturated with hexane. The hexane washes were filtered and the filtrate evaporated under vacuum to give 158 mg of product. 1H NMR (300 MHz, CDCl3): 4.48 (s, 2H), 6.68 (dd, 1H), 6.88 (dd, 1H), 7.11 (m, 5H), 7.36 (m, 3H), 7.50 (dd, 1H).

Workup

  1. customwas obtained (2 hr)
  2. customThe reaction mixture was evaporated under vacuum
  3. customthe residue triturated with hexane
  4. filtrationThe hexane washes were filtered
  5. customthe filtrate evaporated under vacuum

Sources & evidence

ORD record
ord-fdd528b965cc470a956b4af8d34ec523
Source dataset
uspto-grants-1996_12
Patent number
US05583130

Reaction notes

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