4-iodobenzamide

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Crude 4-iodobenzoyl chloride (11.4 g, 42.7 mmol) in THF (75 mL), prepared above, was treated with ammonium hydroxide (5 mL) followed by water (40 mL) at ambient temperature. The reaction mixture was stirred for 3 hours and then partitioned between EtOAc (50 mL) and brine (50 mL). The phases were separated and the organic phase was washed with 10% aqueous NaHCO3 solution (30 mL) and brine (30 mL), dried over Na2SO4, and filtered. The filtrate volume was reduced until a white solid precipitated from solution. The white solid was collected by filtration and washed with diethyl ether to provide the desired product (10.2 g, 41.4 mmol, 97%). partitioned between EtOAc (50 mL) and brine (50 mL) The phases were separated the organic phase was washed with 10% aqueous NaHCO3 solution (30 mL) and brine (30 mL) dried over Na2SO4 filtered precipitated from solution The white solid was collected by filtration washed with diethyl ether

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

Procedure: Crude 4-iodobenzoyl chloride (11.4 g, 42.7 mmol) in THF (75 mL), prepared above, was treated with ammonium hydroxide (5 mL) followed by water (40 mL) at ambient temperature. The reaction mixture was stirred for 3 hours and then partitioned between EtOAc (50 mL) and brine (50 mL). The phases were separated and the organic phase was washed with 10% aqueous NaHCO3 solution (30 mL) and brine (30 mL), dried over Na2SO4, and filtered. The filtrate volume was reduced until a white solid precipitated from solution. The white solid was collected by filtration and washed with diethyl ether to provide the desired product (10.2 g, 41.4 mmol, 97%). partitioned between EtOAc (50 mL) and brine (50 mL) The phases were separated the organic phase was washed with 10% aqueous NaHCO3 solution (30 mL) and brine (30 mL) dried over Na2SO4 filtered precipitated from solution The white solid was collected by filtration washed with diethyl ether

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A suspension of 4-iodobenzamide, pivaldehyde, benzotriazole, and p-toluenesulfonic acid was processed as described in Example IC to provide the title compound.

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

Procedure: The optically pure resin-bound secondary amine resin (from C) was swelled in DCM (200 mL). To the suspension was added pyridine (3.19 g) and then 4-iodobenzoyl chloride (5.3 g, 20.0 millimole). The suspension was shaken overnight. The resin was filtered and washed with 3 portions of DCM, 3 portions of methanol, 3 portions of DCM, and 3 portions of methanol. The resin was dried in vacuo overnight. The resin was filtered washed with 3 portions of DCM, 3 portions of methanol, 3 portions of DCM, and 3 portions of methanol The resin was dried in vacuo overnight

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

Procedure: A total of 20 ml of 15 M ammonium hydroxide was reacted with a solution of 5.4 g p-iodobenzoyl chloride in 25 ml of ether. The crude product was recovered as described in Example 3 and recrystallized from ethanol to yield 3.5 g of p-iodobenzamide as white crystals, m.p. 221°-223°, Rf 0.46. The crude product was recovered recrystallized from ethanol

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

Procedure: A mixture of 2.1 g of 4-iodobenzamide, 30 ml of tetrahydrofuran, and 2 g of Lawesson's reagent was heated to reflux for 1 hour. It was partitioned between toluene and 10% aqueous sodium carbonate solution. The organic phase was dried and evaporated. The crude product was passed over a plug of silica gel using acetone/hexane 1:1 for elution. Crystallization from methylene chloride/hexane gave 1.75 g of yellow crystals with m.p. 163-165° C. was heated to reflux for 1 hour It was partitioned between toluene and 10% aqueous sodium carbonate solution The organic phase was dried evaporated for elution Crystallization from methylene chloride/hexane

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

Procedure: Crude 4-iodobenzoyl chloride (11.4 g, 42.7 mmol) in THF (75 mL), prepared above, was treated with ammonium hydroxide (5 mL) followed by water (40 mL) at ambient temperature. The reaction mixture was stirred for 3 hours and then partitioned between EtOAc (50 mL) and brine (50 mL). The phases were separated and the organic phase was washed with 10% aqueous NaHCO3 solution (30 mL) and brine (30 mL), dried over Na2SO4, and filtered. The filtrate volume was reduced until a white solid precipitated from solution. The white solid was collected by filtration and washed with diethyl ether to provide the desired product (10.2 g, 41.4 mmol, 97%). partitioned between EtOAc (50 mL) and brine (50 mL) The phases were separated the organic phase was washed with 10% aqueous NaHCO3 solution (30 mL) and brine (30 mL) dried over Na2SO4 filtered precipitated from solution The white solid was collected by filtration washed with diethyl ether