Bis-(1H-imidazol-2-YL)-methanone → 6,7-Difluorobenzo[d]isoxazol-3(2h)-one

HRID 245527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245527
[F:1][C:2]1[C:3]([OH:13])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([NH:7]O)=[O:6].C(C1NC=CN=1)(C1NC=CN=1)=O>C1COCC1>[F:12][C:11]1[CH:10]=[CH:9][C:4]2[C:5](=[O:6])[NH:7][O:13][C:3]=2[C:2]=1[F:1]

Komponenten

4

Edukt 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 866581193,4-difluoro-N,2-dihydroxybenzamide2×

Produkt 1

HCID 569462386,7-Difluorobenzo[d]isoxazol-3(2h)-oneAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 3,4-difluoro-N,2-dihydroxybenzamide (Intermediate 527, 7.91 g, 41.8 mmol) and carbonyl diimidazole (13.6 g, 83.7 mmol) in THF (200 ml) was heated at reflux for 90 min. The mixture was partitioned between EtOAC and water and acidified with conc. HCl. The solution was extracted 3 times with EtOAc, each extract being washed with water and brine. Drying (MgSO4) of the combined extracts and removal of solvent gave 6.88 g of product as an off-white solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 90 min
  3. customThe mixture was partitioned between EtOAC and water
  4. extractionThe solution was extracted 3 times with EtOAc
  5. washeach extract being washed with water and brine
  6. customDrying
  7. custom(MgSO4) of the combined extracts and removal of solvent

Quellen und Nachweise

ORD-Eintrag
ord-aaf2e4ebf62843d494d4dce2cd486492
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658641B2

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