Triethylamine → Methyl 5-fluoro-2-isobutyramidobenzoate

HRID 1912517노트

반응식

HRID 1912517 반응식
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13](Cl)(=[O:17])[CH:14]([CH3:16])[CH3:15].C(N(CC)CC)C>O1CCCC1>[F:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 2783401Methyl 2-amino-5-fluorobenzoate

생성물 1

HCID 60787955Methyl 5-fluoro-2-isobutyramidobenzoate수율 51.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of methyl 2-amino-5-fluorobenzoate (alfa) (16.9 g, 100 mmol) and isobutyryl chloride (21.2 g, 200 mmol) in dry tetrahydrofuran was added triethylamine (40.4 g, 400 mmol) at 0° C., then the mixture was stirred at room temperature overnight. After removal of the solvent under reduced pressure, the mixture was suspended in water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The crude product was recrystallized from ethyl acetate/petroleum ether (5:1, 150 mL) to give the title compound as white solid (12.3 g, 51.5%).

후처리

  1. customAfter removal of the solvent under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was recrystallized from ethyl acetate/petroleum ether (5:1, 150 mL)

출처 및 근거

ORD 기록
ord-6981fc5d7a714180ae5e3ee2e7db9fe7
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609674B2

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