반응 #9681

반응 방정식

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

4-bromo-2-fluoroaniline

HCl

→

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

수율 89.4%

용매

n-BuOH

반응 조건

후처리

1. 1
   기타Solvent was removed by rotary evaporation and 1 N aqueous HCl
2. 2
   workup.ADDITIONwas added
3. 3
   기타The aqueous layer was separated
4. 4
   추출extracted with EtOAc
5. 5
   세척The combined organic phases were washed with 1 N aqueous HCl and brine
6. 6
   건조dried over Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   여과the precipitate was collected by filtration
10. 10
    세척washed with MeOH
11. 11
    기타dried in a vacuum oven

실험 절차

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).

출처