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

HRID 6822

Reaktionsgleichung

Reaktionsgleichung von HRID 6822
[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 litres), 2-amino-4-fluoro-5-iodo-benzoic acid (46 grams, 164 mmoles), and trichloromethylchloroformate (97.4 grams, 492 mmoles) were added to a one litre 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 litre of hexanes. The solid was collected by suction filtration, washed with an additional 0.5 litres 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 litres of hexanes
  8. customdried under vacuum at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-0bc8ffdbbaca41bcbaf4c615964c8a93
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084147B2

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