반응 #45648

반응 방정식

hydrochloric acid

trimethylaluminium

methylamine hydrochloride

ethyl-4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

→

compound

수율 64.0%

4-Cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

수율 64.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 63 hours
2. 2
   workup.ADDITIONwas added to the reaction liquid
3. 3
   온도with cooling with ice
4. 4
   workup.STIRRINGby stirring at room temperature
5. 5
   기타The reaction liquid
6. 6
   추출was extracted with chloroform
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   여과filtered
9. 9
   농축the filtrate was concentrated under reduced pressure

실험 절차

Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution, 1.80 ml, 1.85 mmol) was dropwise added to a dichloromethane (2 ml) solution of methylamine hydrochloride (125 mg, 1.85 mmol) at room temperature, and stirred for 40 minutes. Subsequently, a dichloromethane (2 ml) solution of ethyl-4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (200 mg, 617 μl) was dropwise added and stirred for 63 hours. After the reaction, aqueous 1 N hydrochloric acid solution was added to the reaction liquid with cooling with ice, followed by stirring at room temperature. The reaction liquid was extracted with chloroform. Next, the obtained organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with dichloromethane/methanol (100:1, v/v) gave the entitled compound (122 mg, 64%) as a pale green solid.

출처