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

HRID 1053618
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HRID 1053618 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d48087e1205c45a79ba809d86a0940ed
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394240B2

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