31592-84-4

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

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

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 21.3 ml of bromine diluted in 82 ml of acetic acid are added over 6 hours to 84.86 g of N-(3,5-dichlorophenyl)acetamide and 34 g of sodium acetate in 420 ml of acetic acid. After 12 hours at room temperature, the reaction mixture is heated for 5 hours at 50° C. The solvents are evaporated off under reduced pressure. The residue obtained is recrystallized from isopropanol; m.p.=224° C. The solvents are evaporated off under reduced pressure The residue obtained is recrystallized from isopropanol

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

Procedure: 200 ml of pyridine are added dropwise to 100 g of 3,5-dichlorophenylamine in 3000 ml of chloroform, followed by addition of 90 ml of acetic anhydride. The reaction mixture is stirred for 12 hours at room temperature. The solvents are evaporated off under reduced pressure and the residue obtained is recrystallized from 1000 ml of ethyl acetate; m.p.=182° C. The solvents are evaporated off under reduced pressure the residue obtained is recrystallized from 1000 ml of ethyl acetate

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: α-(4-chlorophenyl)-4-pyridinemethanol (0.0512 mol), N-(3,5-dichlorophenyl)-acetamide (0.102 mol) and polyphosphoric acid (210 g) were stirred at 140° C. for 90 minutes. The mixture was cooled to 100° C., poured out into ice water, basified with NH4OH and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was taken up in 2-propanone and diethyl ether. The precipitate was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1). The pure fraction was collected and the solvent was evaporated, yielding 17.94 g (87%) of (±)-N-[3,5-dichloro-4-[(4-chlorophenyl)-4-pyridinylmethyl]phenyl]-acetamide (interm. 28). extracted with CH2Cl2 The organic layer was separated dried filtered the solvent was evaporated The precipitate was filtered off the filtrate was evaporated The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1) The pure fraction was collected the solvent was evaporated

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: α-(4-chlorophenyl)-4-pyridinemethanol (0.0512 mol), N-(3,5-dichlorophenyl)-acetamide (0.102 mol) and polyphosphoric acid (210 g) were stirred at 140° C. for 90 minutes. The mixture was cooled to 100° C., poured out into ice water, basified with NH4OH and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was taken up in 2-propanone and diethyl ether. The precipitate was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1). The pure fraction was collected and the solvent was evaporated, yielding 17.94 g (87%) of (±)-N-[3,5-dichloro-4-[(4-chlorophenyl)-4-pyridinylmethyl]phenyl]-acetamide (interm. 28). extracted with CH2Cl2 The organic layer was separated dried filtered the solvent was evaporated The precipitate was filtered off the filtrate was evaporated The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1) The pure fraction was collected the solvent was evaporated

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

Conditions: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 12 g (58.8 mmole) of N-acetyl-3,5-dichloroaniline, 8.13 g (58.8 mmole) of potassium carbonate (dried at 155° C. under vacuum), 23 g (147 mmole) of bromobenzene (dried over molecular sieves), and 1.12 g (5.9 mmole) of cuprous iodide was heated in a 175° C. oil bath under a reflux condenser under nitrogen for 18 hours. The mixture was cooled to room temperature and triturated with 1 liter of benzene. The solution was concentrated in vacuo. The residue was treated with 50 mL of EtOH and 7.76 g (118 mmole) of potassium hydroxide and the resulting mixture was heated to reflux for two hours. The mixture was cooled and the solvent removed in vacuo. The residue was taken up in 150 mL of hexanes and 20 mL of EtOAc and the resulting solution was washed with 2×100 mL of 2N aqueous HCl and 70 mL of water. The latter wash was back extracted with 60 mL of ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on 200 g of silica gel with 2 liters of 50:1 hexanes:ethyl acetate to give 10 g (71%) of a yellow oil. The mixture was cooled to room temperature triturated with 1 liter of benzene The solution was concentrated in vacuo the resulting mixture was heated to reflux for two hours The mixture was cooled the solvent removed in vacuo 20 mL of EtOAc and the resulting solution was washed with 2×100 mL of 2N aqueous HCl and 70 mL of water The latter wash was back extracted with 60 mL of ethyl acetate the combined organic layers were dried over sodium sulfate filtered concentrated in vacuo The residue was purified by flash chromatography on 200 g of silica gel with 2 liters of 50:1 hexanes

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 21.3 ml of bromine diluted in 82 ml of acetic acid are added over 6 hours to 84.86 g of N-(3,5-dichlorophenyl)acetamide and 34 g of sodium acetate in 420 ml of acetic acid. After 12 hours at room temperature, the reaction mixture is heated for 5 hours at 50° C. The solvents are evaporated off under reduced pressure. The residue obtained is recrystallized from isopropanol; m.p.=224° C. The solvents are evaporated off under reduced pressure The residue obtained is recrystallized from isopropanol

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

Procedure: 200 ml of pyridine are added dropwise to 100 g of 3,5-dichlorophenylamine in 3000 ml of chloroform, followed by addition of 90 ml of acetic anhydride. The reaction mixture is stirred for 12 hours at room temperature. The solvents are evaporated off under reduced pressure and the residue obtained is recrystallized from 1000 ml of ethyl acetate; m.p.=182° C. The solvents are evaporated off under reduced pressure the residue obtained is recrystallized from 1000 ml of ethyl acetate

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: α-(4-chlorophenyl)-4-pyridinemethanol (0.0512 mol), N-(3,5-dichlorophenyl)-acetamide (0.102 mol) and polyphosphoric acid (210 g) were stirred at 140° C. for 90 minutes. The mixture was cooled to 100° C., poured out into ice water, basified with NH4OH and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was taken up in 2-propanone and diethyl ether. The precipitate was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1). The pure fraction was collected and the solvent was evaporated, yielding 17.94 g (87%) of (±)-N-[3,5-dichloro-4-[(4-chlorophenyl)-4-pyridinylmethyl]phenyl]-acetamide (interm. 28). extracted with CH2Cl2 The organic layer was separated dried filtered the solvent was evaporated The precipitate was filtered off the filtrate was evaporated The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1) The pure fraction was collected the solvent was evaporated

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