반응 #90301

반응 방정식

(Z)-2,5-dichloro-N′-hydroxy-4,6-dimethylnicotinimidamide

pyridine

4-hydroxy-3-methoxy-5-nitrobenzoic acid

HCl

→

4-(3-(2,5-dichloro-4,6-dimethylpyridin-3-yl)-1,2,4-oxadiazol-5-yl)-2-methoxy-6-nitrophenol

수율 62.7%

용매

thionyl chloride

반응 조건

후처리

1. 1
   기타The excess of thionyl chloride was removed under vacuum
2. 2
   workup.DISSOLUTIONThe resulting yellow solid was dissolved in DMA (15.4 mL)
3. 3
   온도The red solution was heated to 120° C. for 2.5 hours
4. 4
   온도The reaction mixture was cooled to room temperature
5. 5
   여과The yellow precipitate was filtered off
6. 6
   세척washed with water
7. 7
   기타dried under vacuum
8. 8
   기타Recrystallization from dichloromethane-isopropanol mixture

실험 절차

A stirred suspension of 4-hydroxy-3-methoxy-5-nitrobenzoic acid (2.00 g, 9.38 mmol) in thionyl chloride (8.2 mL) was heated at 80° C. for two hours. The excess of thionyl chloride was removed under vacuum. The resulting yellow solid was dissolved in DMA (15.4 mL), then (Z)-2,5-dichloro-N′-hydroxy-4,6-dimethylnicotinimidamide (2.636 g, 11.26 mmol) and pyridine (6.2 mL) were added. The red solution was heated to 120° C. for 2.5 hours. The reaction mixture was cooled to room temperature and poured into a mixture of cc HCl (10 ml) and ice (80 g), then stirred for thirty minutes. The yellow precipitate was filtered off, washed with water and dried under vacuum. Recrystallization from dichloromethane-isopropanol mixture afforded 2.42 g (62%) of 4-(3-(2,5-dichloro-4,6-dimethylpyridin-3-yl)-1,2,4-oxadiazol-5-yl)-2-methoxy-6-nitrophenol as yellow crystalline.

출처