반응 #45878

반응 방정식

hydrochloric acid

ethyl 6-(3-chlorophenyl)-4-cyano-7-fluoro-5-methyl-1,3-benzoxazole-2-carboxylate

Dimethylamine hydrochloride

trimethylaluminium

→

compound

수율 80.0%

6-(3-Chlorophenyl)-4-cyano-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide

수율 80.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe solution was stirred for 21 hours
2. 2
   온도with gradually heating up to room temperature
3. 3
   workup.WAITtaking 15 minutes
4. 4
   workup.STIRRINGAfter stirring at the same temperature for 30 minutes
5. 5
   기타the reaction liquid
6. 6
   추출was extracted three times with dichloromethane
7. 7
   세척washed with saturated brine
8. 8
   건조dried over anhydrous sodium sulfate
9. 9
   기타The insoluble matter was separated by filtration
10. 10
    기타the solvent was evaporated away
11. 11
    기타the resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform

실험 절차

Dimethylamine hydrochloride (1.406 g, 17.27 mmol) was suspended in dichloromethane (20 ml), and under nitrogen atmosphere at 0° C., trimethylaluminium (1.03 M n-hexane solution) (16.8 ml, 17.27 mmol) was gradually dropwise added. After stirring at room temperature for 30 minutes, a dichloromethane (20 ml) solution of ethyl 6-(3-chlorophenyl)-4-cyano-7-fluoro-5-methyl-1,3-benzoxazole-2-carboxylate (I-310) (2.065 g, 5.75 mmol) was dropwise added at 0° C. The solution was stirred for 21 hours with gradually heating up to room temperature, then at 0° C., aqueous 1 N hydrochloric acid solution (50 ml) was dropwise added, taking 15 minutes. After stirring at the same temperature for 30 minutes, the reaction liquid was extracted three times with dichloromethane. The organic layers were combined, washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform:acetone=99:1, v/v) to obtain the entitled compound (1.641 g, 80%) as a pale yellow solid.

출처