Dimethyl Sulfoxide → Benzeneethanamine, N-phenyl-

HRID 487585Notes

Reaction equation

HRID 487585 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8](Br)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[C:10]1([CH2:9][CH2:8][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6115AnilineHCID 7666Phenethyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 74443Benzeneethanamine, N-phenyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of aniline (9.1 ml, 100 mmol), phenethylbromide 18.5 g, 100 mmol), potassiumcarbonate (13.8 g, 100 mmol) and 50 ml dimethylsulfoxide is stirred at ambient temperature for 72 hours, and is diluted with 200 ml water. The mixture is extracted three times with diethylether and the combined organic phases is washed with water and brine and dried over magnesium sulphate. The solution is concentrated in vacuo and the crude product is subjected to a vacuum distillation yielding the title compound as a colourless oil dest. 120°-128° C./0.7 mbar.

Workup

  1. extractionThe mixture is extracted three times with diethylether
  2. washthe combined organic phases is washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationThe solution is concentrated in vacuo
  5. distillationthe crude product is subjected to a vacuum distillation

Sources & evidence

ORD record
ord-67c4a37d41c44531ba33590a77173983
Source dataset
uspto-grants-1994_03
Patent number
US05296493

Reaction notes

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