Réaction #5938

Équation de réaction

2-aminothiophenol

sodium acetate

methyl α-bromo-4-fluorophenylacetate

→

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

Rendement 87.6%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONAfter the solvent is distilled off
2. 2
   workup.ADDITIONwater is added to the residue
3. 3
   AutreThe resulting precipitate is separated by filtration
4. 4
   Lavagewashed
5. 5
   Autredried
6. 6
   Autrerecrystallized from tetrahydrofuran-n-hexane

Mode opératoire

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.

Source