4-(1-phenylethenyl)aniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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°. The resulting mixture was refluxed for 2 hours cooled The organic phase was washed with 250 ml of water 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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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°. The resulting mixture was refluxed for 2 hours cooled The organic phase was washed with 250 ml of water 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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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°. The resulting mixture was refluxed for 2 hours cooled The organic phase was washed with 250 ml of water 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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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°. The resulting mixture was refluxed for 2 hours cooled The organic phase was washed with 250 ml of water 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