반응 #45768

반응 방정식

Ethyl 3-bromopyruvate

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

sodium hydrogencarbonate

p-toluenesulfonic acid monohydrate

→

compound

수율 91.3%

Ethyl 2-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)-1,3-thiazole-4-carboxylate

수율 91.3%

용매

toluene

water

반응 조건

후처리

1. 1
   온도by heating
2. 2
   온도After cooling to room temperature
3. 3
   온도by heating
4. 4
   온도under reflux in an oil bath at 125° C. for 15 hours
5. 5
   온도After cooling to room temperature
6. 6
   추출followed by extraction with ethyl acetate (50 ml×2)
7. 7
   세척The organic layer was washed with an aqueous saturated sodium hydrogencarbonate solution (50 ml) and saturated brine (50 ml)
8. 8
   건조dried over anhydrous sodium sulfate
9. 9
   농축After concentration
10. 10
    기타the resulting residue was purified by silica gel column chromatography (eluent, chloroform:ethyl acetate=100:1→25:1)

실험 절차

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.

출처