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

HRID 1198453

Reaktionsgleichung

Reaktionsgleichung von HRID 1198453
[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)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 2-aminothiophenol (12.6 g) and o 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 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-ad452b85b99c4164a124b711544a2b08
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281592

Verknüpfte Notizen

Wird geladen…