Azobisisobutyronitrile → HCID 58877917, compound

HRID 597830Notes

Reaction equation

HRID 597830 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[CH3:21])(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:43])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:43][CH2:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[S:11]([N:8]1[CH2:7][CH2:6][N:5]([C:3](=[O:4])[C:2]([F:1])([F:22])[F:23])[CH2:10][CH2:9]1)(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 58877924HCID 58877924, compound

Product 1

HCID 58877917HCID 58877917, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of Intermediate 2 (9.5 g, 27 mmol) in CCl4 (70 mL) was added AIBN (0.5 g, 3 mmol) and the mixture was brought to reflux. NBS (5.3 g, 30 mmol) was added and the mixture was refluxed for 4 h, cooled and filtered to remove solids. Concentration and purification by flash chromatography (0% to 25% EtOAc/hexane) gave the title compound as colorless oil (5.715 g, 49% yield). 1H NMR (300 MHz, CDCl3) δ: 7.65-7.60 (2H, m), 7.33-7.27 (1H, m), 4.83 (2H, s), 3.82-3.79 (2H, m), 3.74-3.71 (2H, m), 3.34-3.30 (4H, m). LCMS (M+H) calcd for C13H14BrF4N2O3S: 433.97; found: 435.11.

Workup

  1. temperatureto reflux
  2. temperaturethe mixture was refluxed for 4 h
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove solids
  6. concentrationConcentration and purification by flash chromatography (0% to 25% EtOAc/hexane)

Sources & evidence

ORD record
ord-a4f12dac45574ed383e4b56c5f985356
Source dataset
uspto-grants-2011_03
Patent number
US07897593B2

Reaction notes

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