Diphosgene → 4-Fluoro-5-iodo-isatoic Anhydride

HRID 51098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51098
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:14]([O:17]C(Cl)=O)(Cl)Cl>O1CCOCC1>[F:11][C:9]1[CH:10]=[C:2]2[NH:1][C:14](=[O:17])[O:6][C:4](=[O:5])[C:3]2=[CH:7][C:8]=1[I:12]

Komponenten

4

Edukt 2

HCID 10426DiphosgeneHCID 219521462-Amino-4-fluoro-5-iodobenzoic acid

Produkt 1

HCID 543357764-Fluoro-5-iodo-isatoic AnhydrideAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Anhydrous dioxane (0.5 liters), 2-amino-4-fluoro-5-iodo-benzoic acid (46 grams, 164 mmoles), and trichloromethylchloroformate (97.4 grams, 492 mmoles) were added to a one liter one neck flask equipped with a magnetic stir bar and reflux condenser. The solution was placed under anhydrous nitrogen, stirred and heated to reflux for 16 hours. The reaction mixture was allowed to cool and was poured into one liter of hexanes. The solid was collected by suction filtration, washed with an additional 0.5 liters of hexanes, and dried under vacuum at room temperature to yield 45.5 grams (90%) of the title compound 1H NMR (400 MHz, DMSO-d6) δ: 11.86(s, 1H), 8.24(d, 1H), 6.84(d, 1H). ESI-MS m/z 308 (M+1).

Aufarbeitung

  1. customequipped with a magnetic stir bar
  2. temperaturereflux condenser
  3. temperatureheated
  4. temperatureto reflux for 16 hours
  5. temperatureto cool
  6. filtrationThe solid was collected by suction filtration
  7. washwashed with an additional 0.5 liters of hexanes
  8. customdried under vacuum at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-1ca824fe34254ad4bacf8c2c60c40b1d
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713485B2

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