Ethyl Acetate → (E)-N-(3-chloro-2-propenyl)-N-ethyl-3-[3-(3-thienyl)benzyloxy]benzylamine

HRID 484544Notes

Reaction equation

HRID 484544 reaction equation
[Cl:1]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)[CH2:6][CH3:7].[H-].[Na+].S(O[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)[CH:25]=1)(=O)(=O)C.C(OCC)(=O)C>O1CCCC1.CN(C)C=O>[Cl:1]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]3[CH:34]=[CH:33][S:32][CH:31]=3)[CH:25]=2)[CH:10]=1)[CH2:6][CH3:7]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 10376384(E)-N-(3-Chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamineHCID 199174863-(3-Thienyl)benzyl mesylate

Product 1

HCID 19917481(E)-N-(3-chloro-2-propenyl)-N-ethyl-3-[3-(3-thienyl)benzyloxy]benzylamineYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 280 mg (1.24 mmol) of (E)-N-(3-chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamine in 2.5 ml of tetrahydrofuran was added 74.4 mg (1.86 mmol) of 60% oily sodium hydride under ice cooling. The mixture was stirred for 20 minutes at room temperature, ice-cooled, treated with a solution of 333 mg (1.24 mmol) of 3-(3-thienyl)benzyl mesylate in 2.5 ml of dimethylformamide, and stirred for 1.5 hours at room temperature. The reaction mixture was poured into 40 ml of ethyl acetate, washed with 20 ml×2 of water and 20 ml of saturated sodium chloride aqueous solut-.ion, dried over anhydrous magnesium sulfate and 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 460 mg (yield: 93%) of the above identified compound as an oil.

Workup

  1. temperatureice-cooled
  2. stirringstirred for 1.5 hours at room temperature
  3. washwashed with 20 ml×2 of water and 20 ml of saturated sodium chloride aqueous solut-.ion
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationconcentrated under reduced pressure
  7. customto obtain 460 mg (yield: 93%) of the

Sources & evidence

ORD record
ord-1eadcfc3c22142d1985ee88956cf5832
Source dataset
uspto-grants-1993_07
Patent number
US05231183

Reaction notes

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