Azobisisobutyronitrile → HCID 16753950, compound

HRID 348126Notes

Reaction equation

HRID 348126 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:7]=1.[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:14][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 16753949HCID 16753949, compound

Product 1

HCID 16753950HCID 16753950, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Under nitrogen, a mixture of intermediate 45, 5-fluoro-2,N,N-trimethyl-benzenesulfonamide, (435 mg, 2.0 mmol) and N-bromosuccinimide (391 mg, 2.2 mmol) in CCl4 (20 mL) was stirred at 80–90° C. for 5 min. To this mixture was added 2,2′-azobisisobutyronitrile (AIBN, 100 mg) and stirring continued at 80–90° C. for 30 min. After cooling, the insoluble precipitates were filtered and the filtrate concentrated and purified by column chromatography (SiO2, CH2Cl2) to provide 440 mg (Yield 74%) of the title compound; 1H NMR (500 MHz, CDCl3) δ ppm: 2.87 (6H, s) 4.86 (2H, s) 7.28 (1H, dd, J=8.55, 2.75 Hz) 7.61–7.65 (2H, m); LC/MC m/z 296/298 (M+H).

Workup

  1. stirringstirring
  2. waitcontinued at 80–90° C. for 30 min
  3. temperatureAfter cooling
  4. customthe insoluble precipitates
  5. filtrationwere filtered
  6. concentrationthe filtrate concentrated
  7. custompurified by column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-b3c5133473cd45cb88307b204c75bf12
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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