Reaktion #59178

Reaktionsgleichung

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

4-bromo-2-fluoroaniline

HCl

→

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

Ausbeute 89.4%

Lösungsmittel

n-BuOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeSolvent was removed by rotary evaporation and 1 N aqueous HCl
2. 2
   workup.ADDITIONwas added
3. 3
   SonstigeThe aqueous layer was separated
4. 4
   Extraktionextracted with EtOAc
5. 5
   WaschenThe combined organic phases were washed with 1 N aqueous HCl and brine
6. 6
   Trocknendried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   Filtrationthe precipitate was collected by filtration
10. 10
    Waschenwashed with MeOH
11. 11
    Sonstigedried in a vacuum oven

Vorschrift

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).

Quelle