4-N,4-N-diethylbenzene-1,4-diamine

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

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

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

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

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

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

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

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

Procedure: A mixture of 26.4 g. (0.122 m.) of the compound of Example I, C. 20 g. (0.122 m.) of N,N-diethyl-p-phenylenediamine and 200 ml. of ethanol was stirred and heated at reflux overnight. The solution was concentrated in vacuo to give 43 g. m.p. 293°-295°. The crude product was recrystallized from 500 ml. of MeOH and precipitated with the addition of 500 ml. of ether. The yield after oven-drying (100°) was 33 g. m.p. 297°-299°. A mixture of 26.4 g heated at reflux overnight The solution was concentrated in vacuo to give 43 g The crude product was recrystallized from 500 ml of MeOH and precipitated with the addition of 500 ml The yield after oven-drying (100°)

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

Procedure: A mixture of 26.4 g. (0.122 m.) of the compound of Example I, C. 20 g. (0.122 m.) of N,N-diethyl-p-phenylenediamine and 200 ml. of ethanol was stirred and heated at reflux overnight. The solution was concentrated in vacuo to give 43 g. m.p. 293°-295°. The crude product was recrystallized from 500 ml. of MeOH and precipitated with the addition of 500 ml. of ether. The yield after oven-drying (100°) was 33 g. m.p. 297°-299°. A mixture of 26.4 g heated at reflux overnight The solution was concentrated in vacuo to give 43 g The crude product was recrystallized from 500 ml of MeOH and precipitated with the addition of 500 ml The yield after oven-drying (100°)

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

Procedure: N,N-diethyl-1,4-phenylenediamine (1.00 g, 6.17 mmol) was added slowly to dilute HCl (700 μl, 32%) in H2O (100 cm3). The mixture was stirred until it was homogeneous. N-[3-(dimethylamino)phenyl]methanesulphonamide (1.32 g, 6.17 mmol) in methanol (60 cm3) was added, followed by a saturated aqueous solution of potassium dichromate (2 cm3). The mixture refluxed for 15 min. The mixture was cooled and diluted with water (200 cm3), acidified with hydrochloric acid (1M) and then extracted with chloroform (6×30 cm3). The combined extracts were dried over sodium sulphate, filtered and the solvent removed under reduced pressure. Column chromatography (1:9 methanol/dichloromethane) gave the target material as a green solid (451 mg, 22%). The mixture refluxed for 15 min The mixture was cooled extracted with chloroform (6×30 cm3) The combined extracts were dried over sodium sulphate filtered the solvent removed under reduced pressure

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

Procedure: N,N-diethyl-1,4-phenylenediamine (1.00 g, 6.17 mmol) was added slowly to dilute HCl (700 μl, 32%) in H2O (100 cm3). The mixture was stirred until it was homogeneous. N-[3-(dimethylamino)phenyl]methanesulphonamide (1.32 g, 6.17 mmol) in methanol (60 cm3) was added, followed by a saturated aqueous solution of potassium dichromate (2 cm3). The mixture refluxed for 15 min. The mixture was cooled and diluted with water (200 cm3), acidified with hydrochloric acid (1M) and then extracted with chloroform (6×30 cm3). The combined extracts were dried over sodium sulphate, filtered and the solvent removed under reduced pressure. Column chromatography (1:9 methanol/dichloromethane) gave the target material as a green solid (451 mg, 22%). The mixture refluxed for 15 min The mixture was cooled extracted with chloroform (6×30 cm3) The combined extracts were dried over sodium sulphate filtered the solvent removed under reduced pressure

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

Procedure: The title compound is prepared analogously as described in Example 105A from (6-chloro-pyrimidin-4-yl)-methyl-amine and 4-amino-N,N-diethylaniline. The ethyl acetate layer is dried over Na2SO4 and evaporated in vacuo. The residue is suspended in CH2Cl2, filtered off and dried to afford the title compound. The title compound is prepared analogously The ethyl acetate layer is dried over Na2SO4 evaporated in vacuo filtered off dried