Hydrochloric Acid → 2-(3-Fluorophenylaminocarbonyl)-7-methoxybenzofuran

HRID 1057939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057939
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[H-].[Na+].[H][H].[CH3:13][O:14][C:15]1[C:23]2[O:22][C:21]([C:24](Cl)=[O:25])=[CH:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:24]([C:21]2[O:22][C:23]3[C:15]([O:14][CH3:13])=[CH:16][CH:17]=[CH:18][C:19]=3[CH:20]=2)=[O:25])[CH:6]=[CH:7][CH:8]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 97423-FluoroanilineHCID 24758Sodium hydrideHCID 227344737-Methoxy-1-benzofuran-2-carbonyl chlorideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 227341942-(3-Fluorophenylaminocarbonyl)-7-methoxybenzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under a nitrogen atmosphere, 3-fluoroaniline (6.2 ml) was dissolved in dry THF (150 ml), and the solution was stirred at 0° C. Sodium hydride (3.4 g) was slowly added to the mixture followed by stirring at 0° C. for 20 minutes. After the generation of hydrogen ceased, 7-methoxybenzofuran-2-carbonyl chloride (9.0 g) was added to the mixture, followed by stirring at room temperature for 3 hours. The reaction was stopped with 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with a 1N aqueous solution of hydrochloric acid and with a saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was triturated with diethyl ether to give Compound IIbf-a (7.82 g, 64.2%) as a white solid.

Aufarbeitung

  1. stirringby stirring at 0° C. for 20 minutes
  2. stirringby stirring at room temperature for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a 1N aqueous solution of hydrochloric acid and with a saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was triturated with diethyl ether
  8. customto give Compound IIbf-a (7.82 g, 64.2%) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-7abd73a2cea644aeb257f1b2f01ecc96
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514996B2

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