Réaction #45583

Équation de réaction

(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

Rendement 85.7%

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

Rendement 85.7%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureunder reflux for 1.5 hours
3. 3
   TempératureAfter cooling
4. 4
   Autrethe reaction liquid
5. 5
   Lavagesuccessively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
6. 6
   Séchagedried on anhydrous magnesium sulfate
7. 7
   Autrethe solvent was evaporated away under reduced pressure
8. 8
   Autreto obtain a pale brown residue
9. 9
   AutreThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Mode opératoire

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.

Source