Reacción #367218

Ecuación de reacción

3,5-diiodosalicylic acid

1-(4-aminophenyl)-1-phenylethylene

phosphorus trichloride

→

N-[4-(1-phenylethenyl)phenyl] -2-hydroxy-3,5-diiodobenzamide

Rendimiento 43.2%

Disolventes

chlorobenzene

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting mixture was refluxed for 2 hours
2. 2
   Temperaturacooled
3. 3
   LavadoThe organic phase was washed with 250 ml of water
4. 4
   Otrodried
5. 5
   OtroThe extract was evaporated to dryness
6. 6
   workup.DISSOLUTIONAfter redissolving the residue in minimum amount of methylene chloride
7. 7
   Otrothe solution was flash-chromatographed on a silica gel column
8. 8
   LavadoThe desired component was eluted with 2 liters of methylene chloride/n-hexane
9. 9
   OtroEvaporation of its solvent

Procedimiento

To a refluxing solution of 7.9 g (0.02 mole) of 3,5-diiodosalicylic acid and 4.6 g (0.02 mole) of 1-(4-aminophenyl)-1-phenylethylene in 125 ml of chlorobenzene was added 3 g (0.022 mole) of phosphorus trichloride over a 1 hour period. The resulting mixture was refluxed for 2 hours, cooled, diluted with 100 ml of methylene chloride. The organic phase was washed with 250 ml of water and dried. The extract was evaporated to dryness. After redissolving the residue in minimum amount of methylene chloride, the solution was flash-chromatographed on a silica gel column. The desired component was eluted with 2 liters of methylene chloride/n-hexane. Evaporation of its solvent gave 4.9 g of N-[4-(1-phenylethenyl)phenyl] -2-hydroxy-3,5-diiodobenzamide. Recrystallization from aqueous ethanol gave 4.2 g of purified product, m.p. 173°-174°.

Fuente