2,6-dichloro-N-phenylaniline

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 l glass reactor was charged with 100 g (0.32 mole) of N-phenyl-2,2,6,6-tetrachlorocyclohexaneimine obtained in Example 1 and 500 g of chlorobenzene, and the mixture was heated in an oil bath with stirring. While keeping the reaction temperature at 100° C., the reaction was continued for 5 hours. After the reaction was completed, the reaction mixture was cooled to 25° C., and washed with 300 g of a 10% aqueous solution of sodium hydroxide. Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure to give 64.7 g of N-phenyl-2,6-dichloroaniline in the state of a black solid (yield: 85%, mp: 49.5° to 50.7° C.). The obtained N-phenyl-2,6-dichloroaniline had a purity of 92.1% measured by means of gas chromatography. the mixture was heated in an oil bath at 100° C. washed with 300 g of a 10% aqueous solution of sodium hydroxide Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure

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

Procedure: A mixture of 2,6-dichlorophenylaniline (810 mg, 5 mmol, Aldrich) and bis(2-chloroethyl)amine hydrochloride (823 mg, 5 mmol, Aldrich) was subjected to microwave irradiation at 200° C. for 10 min. The reaction mixture was allowed to cool to room temperature then treated with 5N NaOH (5 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine (5 mL), dried over Na2SO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water) to give the title compound. MS (ESI, pos. ion) m/z: 231 (M+1). irradiation at 200° C. for 10 min extracted with EtOAc (2×20 mL) The combined organic extracts were washed with brine (5 mL) dried over Na2SO4 filtered The solvent was removed in vacuo the residue was purified by silica gel chromatography eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water)

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

Procedure: A mixture of 2,6-dichlorophenylaniline (810 mg, 5 mmol, Aldrich) and bis(2-chloroethyl)amine hydrochloride (823 mg, 5 mmol, Aldrich) was subjected to microwave irradiation at 200° C. for 10 min. The reaction mixture was allowed to cool to room temperature then treated with 5N NaOH (5 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine (5 mL), dried over Na2SO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water) to give the title compound. MS (ESI, pos. ion) m/z: 231 (M+1). irradiation at 200° C. for 10 min extracted with EtOAc (2×20 mL) The combined organic extracts were washed with brine (5 mL) dried over Na2SO4 filtered The solvent was removed in vacuo the residue was purified by silica gel chromatography eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water)

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

Procedure: A mixture of 2,6-dichlorophenylaniline (810 mg, 5 mmol, Aldrich) and bis(2-chloroethyl)amine hydrochloride (823 mg, 5 mmol, Aldrich) was subjected to microwave irradiation at 200° C. for 10 min. The reaction mixture was allowed to cool to room temperature then treated with 5N NaOH (5 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine (5 mL), dried over Na2SO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water) to give the title compound. MS (ESI, pos. ion) m/z: 231 (M+1). irradiation at 200° C. for 10 min extracted with EtOAc (2×20 mL) The combined organic extracts were washed with brine (5 mL) dried over Na2SO4 filtered The solvent was removed in vacuo the residue was purified by silica gel chromatography eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water)

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

Procedure: A mixture of 2,6-dichlorophenylaniline (810 mg, 5 mmol, Aldrich) and bis(2-chloroethyl)amine hydrochloride (823 mg, 5 mmol, Aldrich) was subjected to microwave irradiation at 200° C. for 10 min. The reaction mixture was allowed to cool to room temperature then treated with 5N NaOH (5 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine (5 mL), dried over Na2SO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water) to give the title compound. MS (ESI, pos. ion) m/z: 231 (M+1). irradiation at 200° C. for 10 min extracted with EtOAc (2×20 mL) The combined organic extracts were washed with brine (5 mL) dried over Na2SO4 filtered The solvent was removed in vacuo the residue was purified by silica gel chromatography eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water)

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 l glass reactor was charged with 100 g (0.32 mole) of N-phenyl-2,2,6,6-tetrachlorocyclohexaneimine obtained in Example 1 and 500 g of chlorobenzene, and the mixture was heated in an oil bath with stirring. While keeping the reaction temperature at 100° C., the reaction was continued for 5 hours. After the reaction was completed, the reaction mixture was cooled to 25° C., and washed with 300 g of a 10% aqueous solution of sodium hydroxide. Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure to give 64.7 g of N-phenyl-2,6-dichloroaniline in the state of a black solid (yield: 85%, mp: 49.5° to 50.7° C.). The obtained N-phenyl-2,6-dichloroaniline had a purity of 92.1% measured by means of gas chromatography. the mixture was heated in an oil bath at 100° C. washed with 300 g of a 10% aqueous solution of sodium hydroxide Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 l glass reactor was charged with 100 g (0.32 mole) of N-phenyl-2,2,6,6-tetrachlorocyclohexaneimine obtained in Example 1 and 500 g of chlorobenzene, and the mixture was heated in an oil bath with stirring. While keeping the reaction temperature at 100° C., the reaction was continued for 5 hours. After the reaction was completed, the reaction mixture was cooled to 25° C., and washed with 300 g of a 10% aqueous solution of sodium hydroxide. Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure to give 64.7 g of N-phenyl-2,6-dichloroaniline in the state of a black solid (yield: 85%, mp: 49.5° to 50.7° C.). The obtained N-phenyl-2,6-dichloroaniline had a purity of 92.1% measured by means of gas chromatography. the mixture was heated in an oil bath at 100° C. washed with 300 g of a 10% aqueous solution of sodium hydroxide Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure

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

Procedure: 37.6 g of 2,4,6-trimethyl phenol and 11 g of sodium hydroxide were dissolved in 30 ml of water and mixed with 150 ml of toluene. The toluene recovered from heating was mixed with 139 ml of N,N-dimethylformamide to obtain a N,N-dimethylformamide solution. 40 g of 2,6-dichlorophenol was dissolved in 130 ml of toluene, followed by the addition of 9.8 g of sodium hydroxide in 20 ml of water, 41.5 g of N-phenyl chloroacetamide and 8.7 ml of N,N-dimethylformamide, and refluxed in a oil bath at 140°-150° C. for 15 h. The toluene was recovered from the reflux, and mixed with the above N,N-dimethylformamide solution and reacted for 3 h. Recovering N,N-dimethylformamide from the reacted mixture with distillation under reduced pressure (145°-150° C., 8 mm Hg) resulted in the formation of 53 g of N-phenyl 2,6-dichloroaniline and the product yield was 90.75%. The toluene recovered from heating was mixed with 139 ml of N,N-dimethylformamide to obtain a N,N-dimethylformamide solution refluxed in a oil bath at 140°-150° C. for 15 h The toluene was recovered from the reflux mixed with the above N,N-dimethylformamide solution reacted for 3 h Recovering N,N-dimethylformamide from the reacted mixture with distillation under reduced pressure (145°-150° C., 8 mm Hg)

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

Procedure: 37.6 g of 2,4,6-trimethyl phenol and 11 g of sodium hydroxide were dissolved in 30 ml of water and mixed with 150 ml of toluene. The toluene recovered from heating was mixed with 139 ml of N,N-dimethylformamide to obtain a N,N-dimethylformamide solution. 40 g of 2,6-dichlorophenol was dissolved in 130 ml of toluene, followed by the addition of 9.8 g of sodium hydroxide in 20 ml of water, 41.5 g of N-phenyl chloroacetamide and 8.7 ml of N,N-dimethylformamide, and refluxed in a oil bath at 140°-150° C. for 15 h. The toluene was recovered from the reflux, and mixed with the above N,N-dimethylformamide solution and reacted for 3 h. Recovering N,N-dimethylformamide from the reacted mixture with distillation under reduced pressure (145°-150° C., 8 mm Hg) resulted in the formation of 53 g of N-phenyl 2,6-dichloroaniline and the product yield was 90.75%. The toluene recovered from heating was mixed with 139 ml of N,N-dimethylformamide to obtain a N,N-dimethylformamide solution refluxed in a oil bath at 140°-150° C. for 15 h The toluene was recovered from the reflux mixed with the above N,N-dimethylformamide solution reacted for 3 h Recovering N,N-dimethylformamide from the reacted mixture with distillation under reduced pressure (145°-150° C., 8 mm Hg)

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 l glass reactor was charged with 100 g (0.32 mole) of N-phenyl-2,2,6,6-tetrachlorocyclohexaneimine obtained in Example 1 and 500 g of chlorobenzene, and the mixture was heated in an oil bath with stirring. While keeping the reaction temperature at 100° C., the reaction was continued for 5 hours. After the reaction was completed, the reaction mixture was cooled to 25° C., and washed with 300 g of a 10% aqueous solution of sodium hydroxide. Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure to give 64.7 g of N-phenyl-2,6-dichloroaniline in the state of a black solid (yield: 85%, mp: 49.5° to 50.7° C.). The obtained N-phenyl-2,6-dichloroaniline had a purity of 92.1% measured by means of gas chromatography. the mixture was heated in an oil bath at 100° C. washed with 300 g of a 10% aqueous solution of sodium hydroxide Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure

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

Procedure: A mixture of 2,6-dichlorophenylaniline (810 mg, 5 mmol, Aldrich) and bis(2-chloroethyl)amine hydrochloride (823 mg, 5 mmol, Aldrich) was subjected to microwave irradiation at 200° C. for 10 min. The reaction mixture was allowed to cool to room temperature then treated with 5N NaOH (5 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine (5 mL), dried over Na2SO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water) to give the title compound. MS (ESI, pos. ion) m/z: 231 (M+1). irradiation at 200° C. for 10 min extracted with EtOAc (2×20 mL) The combined organic extracts were washed with brine (5 mL) dried over Na2SO4 filtered The solvent was removed in vacuo the residue was purified by silica gel chromatography eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water)

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

Procedure: A mixture of 2,6-dichlorophenylaniline (810 mg, 5 mmol, Aldrich) and bis(2-chloroethyl)amine hydrochloride (823 mg, 5 mmol, Aldrich) was subjected to microwave irradiation at 200° C. for 10 min. The reaction mixture was allowed to cool to room temperature then treated with 5N NaOH (5 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine (5 mL), dried over Na2SO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water) to give the title compound. MS (ESI, pos. ion) m/z: 231 (M+1). irradiation at 200° C. for 10 min extracted with EtOAc (2×20 mL) The combined organic extracts were washed with brine (5 mL) dried over Na2SO4 filtered The solvent was removed in vacuo the residue was purified by silica gel chromatography eluting with 10% MeOH/CH2Cl2+1% ammonia (30% in water)