反応 #59161

反応方程式

HCl

isoamyl nitrite

6-trifluoromethoxy-1,3-benzothiazol-2-ylamine

→

desired compound

2-Chloro-6-trifluoromethoxy-1,3-benzothiazole

溶媒

acetonitrile

反応条件

後処理

1. 1
   workup.ADDITIONTo this suspension was added dropwise
2. 2
   workup.STIRRINGThe reaction mixture was stirred at rt for 10 minutes
3. 3
   温度heated at 50° C. for 3 h
4. 4
   温度The mixture was cooled to rt
5. 5
   抽出extracted with ethyl acetate
6. 6
   洗浄The organic layer was washed with 1N aqueous HCl and brine
7. 7
   濃縮concentrated under reduced pressure

実験手順

To a solution containing dry copper (II) chloride (3.44 g, 25.62 mmol) and tri(ethylene glycol)dimethyl ether (10 g) in acetonitrile (150 mL) was added isoamyl nitrite (4.5 mL, 32.02 mmol). The reaction mixture was stirred at rt under argon for 30 minutes. To this suspension was added dropwise, a solution containing 6-trifluoromethoxy-1,3-benzothiazol-2-ylamine (5 g, 21.35 mmol) and tri(ethylene glycol)dimethyl ether (10 g). The reaction mixture was stirred at rt for 10 minutes, and then heated at 50° C. for 3 h. The mixture was cooled to rt, poured cautiously into aqueous 6 N HCl, and extracted with ethyl acetate. The organic layer was washed with 1N aqueous HCl and brine, and concentrated under reduced pressure to give the desired compound in near-quantitative yield, which was used without further purification in the next step.

出典