Reacción #5938

Ecuación de reacción

2-aminothiophenol

sodium acetate

methyl α-bromo-4-fluorophenylacetate

→

2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine

Rendimiento 87.6%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONAfter the solvent is distilled off
2. 2
   workup.ADDITIONwater is added to the residue
3. 3
   OtroThe resulting precipitate is separated by filtration
4. 4
   Lavadowashed
5. 5
   Otrodried
6. 6
   Otrorecrystallized from tetrahydrofuran-n-hexane

Procedimiento

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.

Fuente