Réaction #59178

Équation de réaction

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

4-bromo-2-fluoroaniline

HCl

→

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

Rendement 89.4%

Solvants

n-BuOH

Conditions de réaction

Traitement

1. 1
   AutreSolvent was removed by rotary evaporation and 1 N aqueous HCl
2. 2
   workup.ADDITIONwas added
3. 3
   AutreThe aqueous layer was separated
4. 4
   Extractionextracted with EtOAc
5. 5
   LavageThe combined organic phases were washed with 1 N aqueous HCl and brine
6. 6
   Séchagedried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   Filtrationthe precipitate was collected by filtration
10. 10
    Lavagewashed with MeOH
11. 11
    Autredried in a vacuum oven

Mode opératoire

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).

Source