反応 #9681

反応方程式

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

4-bromo-2-fluoroaniline

HCl

→

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

収率 89.4%

溶媒

n-BuOH

反応条件

後処理

1. 1
   その他Solvent was removed by rotary evaporation and 1 N aqueous HCl
2. 2
   workup.ADDITIONwas added
3. 3
   その他The aqueous layer was separated
4. 4
   抽出extracted with EtOAc
5. 5
   洗浄The combined organic phases were washed with 1 N aqueous HCl and brine
6. 6
   乾燥dried over Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   ろ過the precipitate was collected by filtration
10. 10
    洗浄washed with MeOH
11. 11
    その他dried in a vacuum oven

実験手順

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)-4-methyl-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).

出典