반응 #45616

반응 방정식

6-(2-Bromoacetyl)-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

cesium carbonate

thioacetamide

→

compound

수율 44.2%

2-Cyclopropyl-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

수율 44.2%

용매

toluene

반응 조건

후처리

1. 1
   기타The reaction liquid
2. 2
   온도was cooled
3. 3
   기타the insoluble matter was separated by filtration through Celite, ethyl acetate
4. 4
   workup.ADDITIONwas added to the filtrate
5. 5
   세척by washing with water and saturated brine
6. 6
   건조The obtained organic layer was dried over anhydrous sodium sulfate
7. 7
   기타the solvent was evaporated away under reduced pressure
8. 8
   기타The resulting residue was recrystallized
9. 9
   기타purified with n-hexane/ethyl acetate

실험 절차

6-(2-Bromoacetyl)-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-79) (39.98 g, 28.6 mmol) was dissolved in toluene (270 ml), then cesium carbonate (13.02 g, 39.90 mmol) and thioacetamide (2.58 g, 34.28 mmol) were added, followed by stirring at 100° C. for 6 hours under nitrogen atmosphere. The reaction liquid was cooled, the insoluble matter was separated by filtration through Celite, ethyl acetate was added to the filtrate, followed by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (3.96 g, 44%) as a white solid.

출처