تفاعل #45616

معادلة التفاعل

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

cesium carbonate

thioacetamide

→

compound

المردود 44.2%

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

المردود 44.2%

المذيبات

toluene

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر