Ethyl Bromide → N-(2-Ethoxyethyl)-N-methylaniline

HRID 2184082Notes

Reaction equation

HRID 2184082 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][OH:5].[OH-].[K+].[CH2:14](Br)[CH3:15]>CS(C)=O.O>[CH2:14]([O:5][CH2:4][CH2:3][N:2]([CH3:1])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:15]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 14797Potassium HydroxideHCID 623402-(N-Methylanilino)ethanol

Product 1

HCID 22475607N-(2-Ethoxyethyl)-N-methylanilineYield 95%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of the product from step 1 (850 mg, 506 mmol) in DMSO (4 mL) and KOH (1.2 g, 22.0 mmol) was added ethyl bromide (0.85 mL, 11.4 mmol). After stirring 1.5 hours at ambient temperature, the reaction mixture was diluted with water and the product extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered and concentrated to afford the title compound as a yellow oil (950 mg, 95%). MS (ES+) m/z 180 (MH+).

Workup

  1. extractionthe product extracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a5b326bb571546e2996edefcd7b42511
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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