Water → N-(4-bromobenzyl)diphenylamine

HRID 1058644Notes

Reaction equation

HRID 1058644 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.[H-].[Na+].O>CN(C)C=O>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11487DiphenylamineHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromide

Product 1

HCID 18669015N-(4-bromobenzyl)diphenylamineYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an argon atmosphere, diphenylamine (338 mg, 2.00 mmol) and 4-bromobenzyl bromide (500 mg, 2.00 mmol) were dissolved in dimethylformamide (8 mL), and to the solution was added sodium hydride (88 mg, 2.2 mmol) under ice -cooling, followed by stirring at room temperature for 4 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (14:1 hexane/acetone) to obtain N-(4-bromobenzyl)diphenylamine (478 mg, 71%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (14:1 hexane/acetone)

Sources & evidence

ORD record
ord-691b9882a8c84e1091274a54d9424759
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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