Azobisisobutyronitrile → HCID 21069850, compound

HRID 1788136Notes

Reaction equation

HRID 1788136 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:10]([F:13])([F:12])[F:11])[N:9]=[N:8]2)[CH:2]=1.[Br:15]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:14][C:1]1[CH:2]=[C:3]([C:7]2([C:10]([F:12])([F:11])[F:13])[N:9]=[N:8]2)[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 21069869HCID 21069869, compound

Product 1

HCID 21069850HCID 21069850, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of intermediate 63, 3-m-tolyl-3-trifluoromethyl-3H-diazirine, (200 mg, 1 mmol) in CCl4 (4 mL) was added N-bromosuccinimide (200 mg, 1.1 mmol, re-crystallized from water), and the stirred mixture heated at 85° C. To this was added AIBN (50 mg) and the mixture heated at reflux for an additional 2.5 hrs. After cooling, the mixture was purified by column chromatography (SiO2, pentane) to provide 150 mg (Yield 54%) of the title compound as a clear oil. 1H NMR (300 MHz, CDCl3) δ ppm: 4.42 (2 H, s) 7.10-7.17 (2 H, m) 7.31-7.45 (2 H, m).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for an additional 2.5 hrs
  3. temperatureAfter cooling
  4. customthe mixture was purified by column chromatography (SiO2, pentane)

Sources & evidence

ORD record
ord-7965cd4c675942eaa86bbab692b71822
Source dataset
uspto-grants-2009_03
Patent number
US07511037B2

Reaction notes

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