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

HRID 1708686ノート

反応式

HRID 1708686 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 280 mg (1.24 mmol) of (E)-N-(3-chloro-2-propenyl)-N-ethyl-3-hydroxybenzyiamine 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.

後処理

  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

出典と根拠

ORDレコード
ord-4f9c2f373aff4c1eb84d0a70fff51baa
出典データセット
uspto-grants-1994_10
特許番号
US05359091

反応ノート

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