反应 #9663

反应方程式

HCl

isoamyl nitrite

4,6-difluoro-1,3-benzothiazol-2-amine

→

2-chloro-4,6-difluoro-1,3-benzothiazole

收率 99.0%

溶剂

acetonitrile

—

tri(ethylene glycol) dimethyl ether

反应条件

后处理

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 10 minutes
2. 2
   温度heated at 50° C. for 2.5 h
3. 3
   温度The reaction mixture was cooled to rt
4. 4
   萃取The solution was extracted with EtOAc
5. 5
   洗涤The organic layer was washed with HCl (1.0 M), water and brine
6. 6
   过滤filtered
7. 7
   浓缩concentrated down

实验过程

To a solution containing copper chloride (II) (0.87 g, 6.45 mmol) and tri(ethylene glycol) dimethyl ether (3 mL) in acetonitrile (50 mL) was added isoamyl nitrite (0.94 g, 8.06 mmol), and the reaction mixture was stirred at rt for 30 minutes. To this suspension was added dropwise a solution of 4,6-difluoro-1,3-benzothiazol-2-amine (1.0 g, 5.37 mmol) in tri(ethylene glycol) dimethyl ether (5 mL). The reaction mixture was stirred at rt for 10 minutes, and then heated at 50° C. for 2.5 h. The reaction mixture was cooled to rt, and then poured cautiously into cold aqueous 6 M HCl (200 mL). The solution was extracted with EtOAc. The organic layer was washed with HCl (1.0 M), water and brine, filtered and concentrated down to afford 2-chloro-4,6-difluoro-1,3-benzothiazole (1.1 g, 99%). 1H NMR (400 MHz, DMSO-d6) 7.05 (m, 1H), 7.36 (m, 1H).

来源