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

HRID 1648627

반응식

HRID 1648627 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

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 solution, 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.

후처리

  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 solution
  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

출처 및 근거

ORD 기록
ord-64aa04a673394c628bbd0698f57caad2
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05436354

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