Thionyl Chloride → 5,6-difluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 1378008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378008
S(Cl)(Cl)=O.C([O:9][C:10]([NH:12][C:13]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[C:14]=1[C:15]([OH:17])=[O:16])=O)(C)(C)C>O1CCCC1>[F:23][C:18]1[C:14]2[C:15](=[O:17])[O:16][C:10](=[O:9])[NH:12][C:13]=2[CH:21]=[CH:20][C:19]=1[F:22]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 229144216-((tert-Butoxycarbonyl)amino)-2,3-difluorobenzoic acid

Produkt 1

HCID 229144245,6-difluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 108 ml of thionyl chloride in 300 ml of tetrahydrofuran was added dropwise while cooling with ice to a solution of 100 g (366 mmol) of 2-(tert.-butoxycarbonyl)amino-5,6-difluorobenzoic acid in 1.5 I of dry tetrahydrofuran, whereupon the mixture was stirred at room temperature for 16 hours. The brown solution was evaporated and the brown solid obtained was triturated with methylene chloride. The beige powder obtained was filtered off and dried in a high vacuum. There were obtained 56.5 g (77%) of 5,6-difluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione as a beige powder of m.p. >240°.

Aufarbeitung

  1. customThe brown solution was evaporated
  2. customthe brown solid obtained
  3. customwas triturated with methylene chloride
  4. customThe beige powder obtained
  5. filtrationwas filtered off
  6. customdried in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-67f724e6c1e6457ebc0811b18188936c
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665718

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