Azobisisobutyronitrile → [2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromide

HRID 1647927Notes

Reaction equation

HRID 1647927 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[S:14]([NH:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])=[O:15])=[CH:4][CH:3]=1.[Br:22]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:22][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[S:14]([NH:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 152820992'-(N-t-Butylsulfamoyl)-4-methylbiphenyl

Product 1

HCID 15282100[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromideYield 140.9%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5.0 g (16.5 mmol) of 4-methyl-2'-(t-butylaminosulfonyl)-1,1'-biphenyl in 400 mL of carbon tetrachloride was added 2.35 g (13.2 mmol, 0.8eq) of recrystallized N-bromosuccinimide and 27.5 mg of azobisisobutyronitrile (AIBN). The mixture was refluxed under a nitrogen amosphere for 4 hours at which time an additional 1.17 g (6.57 mmol, 0.40 eq) of N-bromosuccinimide and a trace of AIBN were added and refluxing continued for another 2 hours. The mixture was cooled to room temperature, filtered and the filtrate concentrated to dryness to give 7.11 g of crude product which was used without further purification. 1H NMR (200 MHz, CDCl3): δ 1.07 (s, 9H), 3.63 (br s, 1H), 4.60 (s, 2H), 7.3-7.7 (m,7H), 8.11 (dd; 2, 8 Hz; 1H). FAB-MS: calculated for C17H20BrNO2S 381; found 382 (M+H, 2.5%).

Workup

  1. temperaturerefluxing
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-3af767219228417d84b3044844c30b9c
Source dataset
uspto-grants-1995_07
Patent number
US05434261

Reaction notes

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