반응 #45901

반응 방정식

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

triethylamine

4-Methoxybenzylamine

→

compound

수율 49.0%

4-Cyano-7-(4-methoxybenzylamino)-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

수율 49.0%

용매

dimethyl sulfoxide

반응 조건

후처리

1. 1
   기타The reaction liquid
2. 2
   온도was cooled to room temperature
3. 3
   기타the solvent was evaporated away under reduced pressure
4. 4
   건조the organic layer was dried over anhydrous sodium sulfate
5. 5
   기타The insoluble matter was separated by filtration
6. 6
   기타the solvent was evaporated away
7. 7
   기타the resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform

실험 절차

4-Cyano-7-fluoro-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-114) (1.0 g, 3-09 mmol) was dissolved in dimethyl sulfoxide (60 ml), then at room temperature, triethylamine (560 μl, 4.02 mmol) was added, followed by heating at 150° C. 4-Methoxybenzylamine (525 μl, 4.02 mmol) was added to the solution all at a time, followed by stirring for 1.5 hours. The reaction liquid was cooled to room temperature, and the solvent was evaporated away under reduced pressure. The residue was fractionated with chloroform and saturated brine, and the organic layer was 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=98:2, v/v) to obtain the entitled compound (665 mg, 49%) as a yellow solid.

출처