Reaktion #599746

Reaktionsgleichung

2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic ac id

2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic acid

6-(trifluoromethyl)-2-aminobenzothiazole

1-Ethyl-3-(3-Dimethylaminopropyl)carbodiimide

1-hydroxy-1,2,3-benzotriazole

→

product ( 8i )

N1-[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]-2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxy phenyl)-1-ethenyl]phenoxy}acetamide

Lösungsmittel

water

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane
2. 2
   SonstigeThe solvent was evaporated under vacuum
3. 3
   Sonstigeto afford the crude product
4. 4
   SonstigeThis was further purified by column chromatography

Vorschrift

To a solution of 6-(trifluoromethyl)-2-aminobenzothiazole (218 mg, 1.0 mmol) in dichloromethane (20 mL) was added 1-Ethyl-3-(3-Dimethylaminopropyl)carbodiimide (EDC) (191 mg, 1.0 mmol) and 1-hydroxy-1,2,3-benzotriazole (HOBt) (13.5 mg, 0.1 mmol). Then added 2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic ac id (1) (374 mg, 0.1 mmol) and the reaction mixture was stirred at a temperature of 25° C. for 24 h and the reaction was monitored by TLC. Then to this water is added and extracted with dichloromethane. The solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate and hexane as solvent system to obtain the pure product (8i) (450 mg, 80% yield)

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