تفاعل #45768
ord-1171c5d92c7945a39487ce52620c7f22
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1درجة الحرارةby heating
- 2درجة الحرارةAfter cooling to room temperature
- 3درجة الحرارةby heating
- 4درجة الحرارةunder reflux in an oil bath at 125° C. for 15 hours
- 5درجة الحرارةAfter cooling to room temperature
- 6استخلاصfollowed by extraction with ethyl acetate (50 ml×2)
- 7غسيلThe organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution (50 ml) and saturated brine (50 ml)
- 8تجفيفdried over anhydrous sodium sulfate
- 9تركيزAfter concentration
- 10أخرىthe resulting residue was purified by silica gel column chromatography (eluent, chloroform:ethyl acetate=100:1→25:1)
الإجراء التجريبي
Ethyl 3-bromopyruvate (72.2 μl, 0.518 mmol) was added to a toluene (10 ml) solution of 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carbothioamide (I-196-1) (124 mg, 0.398 mmol), followed by heating under reflux in an oil bath at 125° C. for 2 hours. After cooling to room temperature, p-toluenesulfonic acid monohydrate (15.2 mg, 0.080 mmol) was added to the reaction liquid, followed by heating under reflux in an oil bath at 125° C. for 15 hours. After cooling to room temperature, an aqueous saturated sodium hydrogencarbonate solution (50 ml) and water (50 ml) were added, followed by extraction with ethyl acetate (50 ml×2). The organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution (50 ml) and saturated brine (50 ml), and dried over anhydrous sodium sulfate. After concentration, the resulting residue was purified by silica gel column chromatography (eluent, chloroform:ethyl acetate=100:1→25:1) to obtain the entitled compound (148 mg, 91.2%) as a pale yellow solid.