반응 #9664

반응 방정식

HCl

isoamyl nitrite

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

→

desired compound

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

용매

acetonitrile

반응 조건

후처리

1. 1
   workup.ADDITIONTo this suspension was added dropwise
2. 2
   workup.STIRRINGThe reaction mixture was stirred at rt for 10 minutes
3. 3
   온도heated at 50° C. for 3 h
4. 4
   온도The mixture was cooled to rt
5. 5
   추출extracted with ethyl acetate
6. 6
   세척The organic layer was washed with 1N aqueous HCl and brine
7. 7
   농축concentrated under reduced pressure

실험 절차

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.

출처