Reaktion #367218

Reaktionsgleichung

3,5-diiodosalicylic acid

1-(4-aminophenyl)-1-phenylethylene

phosphorus trichloride

→

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

Ausbeute 43.2%

Lösungsmittel

chlorobenzene

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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°.

Quelle