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Water → methyl 3-(N-ethylbenzamido)-2-fluorobenzoate

HRID 534671
ノート
印刷プレビュー

反応式

HRID 534671 の反応式
[C:1]([NH:9][C:10]1[C:11]([F:20])=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:23](I)[CH3:24].O>CN(C)C=O>[CH2:23]([N:9]([C:10]1[C:11]([F:20])=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])[C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 58298651Methyl 3-benzamido-2-fluorobenzoate

生成物 1

HCID 58298652methyl 3-(N-ethylbenzamido)-2-fluorobenzoate収率 61.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Methyl 3-benzamido-2-fluorobenzoate (3.10 g, 11.0 mmol) was dissolved in N,N-dimethylformamide (30 ml), and the solution was cooled. 60% Sodium hydride (0.53 g, 13.2 mmol) was added thereto, and the reaction mixture was agitated without heating or cooling. 10 minutes later, ethyl iodide (2.05 g, 13.0 mmol) was added to the mixture, and the mixture was agitated overnight at room temperature. Water was added dropwise to the reaction mixture, and the reaction mixture was extracted with ethyl acetate, and dried over anhydrous sodium sulfate. The sodium sulfate was filtered away, and then the filtrate was concentrated under reduced pressure. The concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/5), as a result of which 2.03 g (yield: 61%) of the indicated compound was obtained.

後処理

  1. temperaturethe solution was cooled
  2. temperaturewithout heating
  3. temperaturecooling
  4. stirringthe mixture was agitated overnight at room temperature
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe sodium sulfate was filtered away
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/5)

出典と根拠

ORDレコード
ord-62822ae281ea44968493964a42b78f51
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08853440B2

反応ノート

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