Ethyl Acetate → (E)-N-(3-Chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamine

HRID 1648611Notes

Reaction equation

HRID 1648611 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[CH3:2].[Cl:12][CH:13]=[CH:14][CH2:15]Cl.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O>[Cl:12]/[CH:13]=[CH:14]/[CH2:15][N:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 248831,3-DichloropropeneHCID 100576883-((Ethylamino)methyl)phenol

Product 1

HCID 10376384(E)-N-(3-Chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamineYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 34.96 g (0.231 moi) of N-ethyl-3-hydroxybenzylamine in 200 ml of dimethylsulfoxide were added 25.64 g (0.231 mol) of 1,3-dichloropropene (E/Z=2/1) and 16.7 g (0.121 mol) of ground potassium carbonate under ice cooling. The mixture was stirred for 4 hours at 50° C., poured into 250 ml of ethyl acetate, washed with 200 ml ×2 of water and 200 ml of saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to-silica gel chromatography (n-hexane→n-hexane/ethyl acetate =9/1). The desired fractions were put together and concentrated under reduced pressure to obtain 26.2 g (yield: 50%) of the above identified compound as an oil.

Workup

  1. washwashed with 200 ml ×2 of water and 200 ml of saturated sodium chloride aqueous solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. concentrationconcentrated under reduced pressure
  5. customto obtain 26.2 g (yield: 50%) of the

Sources & evidence

ORD record
ord-88ee3ecf77584c3b9e5fe18705b509f0
Source dataset
uspto-grants-1995_07
Patent number
US05436354

Reaction notes

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