Reacción #59178

Ecuación de reacción

2-chloro-4-methyl-1,3-benzothiazole

4-bromo-2-fluoroaniline

HCl

→

N-(4-bromo-2-fluorophenyl)-4methyl-1,3-benzothiazol-2-amine

Rendimiento 89.4%

Disolventes

n-BuOH

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSolvent was removed by rotary evaporation and 1 N aqueous HCl
2. 2
   workup.ADDITIONwas added
3. 3
   OtroThe aqueous layer was separated
4. 4
   Extracciónextracted with EtOAc
5. 5
   LavadoThe combined organic phases were washed with 1 N aqueous HCl and brine
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Filtraciónthe precipitate was collected by filtration
10. 10
    Lavadowashed with MeOH
11. 11
    Otrodried in a vacuum oven

Procedimiento

To a solution of 2-chloro-4-methyl-1,3-benzothiazole (0.25 g, 1.36 mmol) in n-BuOH (8 mL was added 4-bromo-2-fluoroaniline (0.52 g, 2.72 mmol) and HCl (4.0 M in dioxane, 0.5 mL). The reaction was heated at 90° C. overnight. Solvent was removed by rotary evaporation and 1 N aqueous HCl was added. The aqueous layer was separated and extracted with EtOAc. The combined organic phases were washed with 1 N aqueous HCl and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was brought up in MeOH and the precipitate was collected by filtration, washed with MeOH, and dried in a vacuum oven to give N-(4-bromo-2-fluorophenyl)-4methyl-1,3-benzothiazol-2-amine (0.41 g, 89%). 1H NMR (400 MHz, DMSO-d6) δ 2.62 (s, 3H), 7.07 (t, 1H), 7.15 (d, 1H), 7.36 (m, 2H), 7.51 (d, 1H), 8.72 (t, 1H).

Fuente