2-Aminothiophenol → 2-(4-Fluorophenyl)-2H-1,4-benzothiazin-3(4H)-one

HRID 1439865

Reaktionsgleichung

Reaktionsgleichung von HRID 1439865
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C([O-])(=O)C.[Na+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:16](OC)=[O:17]>C(O)C>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH:15]2[C:16](=[O:17])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]2)=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 87132-AminothiophenolHCID 517045Sodium AcetateHCID 12717580Methyl 2-bromo-2-(4-fluorophenyl)acetate

Produkt 1

HCID 136907612-(4-Fluorophenyl)-2H-1,4-benzothiazin-3(4H)-oneAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 2-aminothiophenol (12.6 g) and sodium acetate (23.6 g) in ethanol (150 ml) is added methyl α-bromo-4-fluorophenylacetate (23.6 g), and the mixture is stirred at room temperature overnight. After the solvent is distilled off, water is added to the residue. The resulting precipitate is separated by filtration, washed, dried, and then recrystallized from tetrahydrofuran-n-hexane to give 2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine (21.7 g) as crystals. M.p. 216°-219° C.

Aufarbeitung

  1. distillationAfter the solvent is distilled off
  2. additionwater is added to the residue
  3. customThe resulting precipitate is separated by filtration
  4. washwashed
  5. customdried
  6. customrecrystallized from tetrahydrofuran-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-5e2a977b30994d0bba62d64549e513b5
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05496815

Verknüpfte Notizen

Wird geladen…