Water → Benzenemethanamine, N-phenyl-N-(phenylmethyl)-

HRID 2248834Notes

Reaction equation

HRID 2248834 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+].O>CS(C)=O>[CH2:8]([N:1]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 7498Benzyl BromideHCID 516892Sodium Bicarbonate

Product 1

HCID 66681Benzenemethanamine, N-phenyl-N-(phenylmethyl)-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred solution of 93.1 g (1 mole) of aniline, 342.1 g (2 mole) of benzyl bromide, and 252 g (3 mole) of sodium bicarbonate in dimethylsulfoxide is heated at 90° C. for three hours. After cooling to room temperature, the reaction mixture is poured into a four-fold excess of water, and the aqueous solution is extracted with methylene chloride. The combined organics are filtered through cotton and evaporated to yield N,N-dibenzylaniline, which is purified by flash chromatography.

Workup

  1. extractionthe aqueous solution is extracted with methylene chloride
  2. filtrationThe combined organics are filtered through cotton
  3. customevaporated

Sources & evidence

ORD record
ord-9e1f8b1161fe4993bd484c908e04d1b2
Source dataset
uspto-grants-1991_08
Patent number
US05041510

Reaction notes

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