Sodium Bicarbonate → HCID 89443836, Verbindung

HRID 1771715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771715
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:11]=1)[C:6]([OH:8])=O)#[N:2].[NH2:19][C:20]1[C:21]([F:28])=[C:22]([OH:27])[CH:23]=[CH:24][C:25]=1[F:26].C([O-])(O)=O.[Na+]>O=S(Cl)Cl.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:11]=1)[C:6]([NH:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([OH:27])[C:21]=1[F:28])=[O:8])#[N:2]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 227559833-Amino-2,4-difluorophenolHCID 89443880HCID 89443880, Verbindung

Produkt 1

HCID 89443836HCID 89443836, VerbindungAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

3-Cyano-5-(3-fluorophenyl)benzoic acid (500 mg, 2.1 mmol, 1 eq) was dissolved in SOCl2 (15 mL) and heated at reflux overnight. The excess SOCl2 was removed under reduced pressure and the residue that remained dissolved in THF (10 mL) and added dropwise to a mixture of 3-amino-2,4-difluorophenol (280 mg, 2 mmol, 0.95 eq) and NaHCO3 (880 mg, 10.5 mmol, 5 eq) in THF (40 mL). The reaction was stirred at room temperature for 3 h, then filtered and the filtrate concentrated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 10:1) to give the title compound as a white solid (500 mg, 64%).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe excess SOCl2 was removed under reduced pressure
  4. dissolutionthe residue that remained dissolved in THF (10 mL)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by column chromatography (petroleum ether: EtOAc, 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-225847c53064427c885b0b44ca8d4496
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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