Triethylamine → Methyl 5-fluoro-2-isobutyramidobenzoate

HRID 1912517ノート

反応式

HRID 1912517 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 60787955Methyl 5-fluoro-2-isobutyramidobenzoate収率 51.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-6981fc5d7a714180ae5e3ee2e7db9fe7
出典データセット
uspto-grants-2013_12
特許番号
US08609674B2

反応ノート

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