반응 #45583

반응 방정식

(2-bromo-5-cyano-3-hydroxy-6-methylbiphenyl-4-yl)cyclopropanecarboxamide 4-amino-2-bromo-5-cyano-6-methylbiphenyl-4-yl cyclopropanecarboxylate

p-toluenesulfonic acid monohydrate

toluene

→

compound

수율 85.7%

7-Bromo-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

수율 85.7%

용매

ethyl acetate

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux for 1.5 hours
3. 3
   온도After cooling
4. 4
   기타the reaction liquid
5. 5
   세척successively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
6. 6
   건조dried on anhydrous magnesium sulfate
7. 7
   기타the solvent was evaporated away under reduced pressure
8. 8
   기타to obtain a pale brown residue
9. 9
   기타The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

실험 절차

Next, a mixture of (2-bromo-5-cyano-3-hydroxy-6-methylbiphenyl-4-yl)cyclopropanecarboxamide/4-amino-2-bromo-5-cyano-6-methylbiphenyl-4-yl cyclopropanecarboxylate mixture (160 mg, 0.426 mmol), p-toluenesulfonic acid monohydrate (24 mg, 0.128 mmol) and toluene (13 ml) was heated under reflux for 1.5 hours. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the entitled compound (129 mg) as a colorless solid.

출처