Toluene → HCID 90370296, compound

HRID 1755512Notes

Reaction equation

HRID 1755512 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.[Br:25]N1C(=O)CCC1=O.C1(C)C=CC=CC=1>O>[Br:25][C:4]1[CH:3]=[CH:2][C:1]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 13087228HCID 13087228, compound

Product 1

HCID 90370296HCID 90370296, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a stream of nitrogen, a 100 mL three-necked flask was charged with 15.0 g (61.1 mmol) of N-phenyl-N-biphenylylamine. 100 mL of dimethylformamide and 10.8 g (61.1 mmol) of N-bromosuccinimide were added to the content, and the mixture was stirred at room temperature for 2 hours. To the thus-obtained reaction mixture, 10 mL of toluene and then 10 mL of pure water were added, and the reaction mixture was separated into an organic phase and an aqueous phase. The organic phase was washed with pure water and then with an aqueous saturated sodium chloride solution. The washed organic phase was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The thus-obtained solid was recrystallized from toluene to give 13.4 g (41.4 mmol) of N-(4-bromophenyl)-N-biphenylylamine as a grey powder (yield: 67%).

Workup

  1. customthe reaction mixture was separated into an organic phase
  2. washThe organic phase was washed with pure water
  3. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe thus-obtained solid was recrystallized from toluene

Sources & evidence

ORD record
ord-bec8b85c4b334e38a8bd9669f0312db7
Source dataset
uspto-grants-2015_10
Patent number
US09172045B2

Reaction notes

Loading…