N-(propan-2-ylideneamino)propan-2-imine

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

Procedure: A crude peracetic acid solution was prepared by mixing 17.3 g glacial acetic acid (0.29 mole), 7.2 g of a hydrogen peroxide solution having 68% by weight of H2O2 (0.145 mole of H2O2), and 0.7 g concentrated sulphuric acid, and reacting the mixture for several hours at ambient temperature. A solution was obtained which contained 0.10 mole peracetic acid and 0.033 mole uncoverted hydrogen peroxide, and which was introduced into 200 ml of methanol at 0° C. Within the space of half an hour 34.8 g acetone (0.6 mole), 12.2 g of an ammonia solution having 28% by weight NH3 (0.2 mole), and 18.6 g aniline (0.2 mole) were added, after which the mixture was determined by gas phase chromatography to contain 4.6 g of acetone phenylhydrazone (0.031 mole, which was 31% of the theoretical yield compared to the peracid), 1 g of acetone azine (0.009 mole, which was 9% of the theoretical yield), and 0.025 mole of azobenzene. for several hours at ambient temperature A solution was obtained which were added theoretical yield

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

Procedure: A crude peracetic acid solution was prepared by mixing 17.3 g glacial acetic acid (0.29 mole), 7.2 g of a hydrogen peroxide solution having 68% by weight of H2O2 (0.145 mole of H2O2), and 0.7 g concentrated sulphuric acid, and reacting the mixture for several hours at ambient temperature. A solution was obtained which contained 0.10 mole peracetic acid and 0.033 mole uncoverted hydrogen peroxide, and which was introduced into 200 ml of methanol at 0° C. Within the space of half an hour 34.8 g acetone (0.6 mole), 12.2 g of an ammonia solution having 28% by weight NH3 (0.2 mole), and 18.6 g aniline (0.2 mole) were added, after which the mixture was determined by gas phase chromatography to contain 4.6 g of acetone phenylhydrazone (0.031 mole, which was 31% of the theoretical yield compared to the peracid), 1 g of acetone azine (0.009 mole, which was 9% of the theoretical yield), and 0.025 mole of azobenzene. for several hours at ambient temperature A solution was obtained which were added theoretical yield

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetone azine (1.50 g, 13.4 mmol) was dissolved in 10 mL of diethyl ether, mixed with 32 mL (19.2 mmol) of 0.6 M benzylmagnesium bromide in tetrahydrofuran and stirred at 45° C. for 24 hours. The reaction was quenched with saturated aqueous ammonium chloride (100 ml), and the reaction solution was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using hexane-ethyl acetate (9:1 to 6:1) as the eluent to give 710 mg of the desired product as a pale yellow oil. The reaction was quenched with saturated aqueous ammonium chloride (100 ml) the reaction solution was extracted with ethyl acetate The resulting organic layer was dried over anhydrous magnesium sulfate filtered the filtrate was concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetone azine (1.50 g, 13.4 mmol) was dissolved in 10 mL of diethyl ether, mixed with 32 mL (19.2 mmol) of 0.6 M benzylmagnesium bromide in tetrahydrofuran and stirred at 45° C. for 24 hours. The reaction was quenched with saturated aqueous ammonium chloride (100 ml), and the reaction solution was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using hexane-ethyl acetate (9:1 to 6:1) as the eluent to give 710 mg of the desired product as a pale yellow oil. The reaction was quenched with saturated aqueous ammonium chloride (100 ml) the reaction solution was extracted with ethyl acetate The resulting organic layer was dried over anhydrous magnesium sulfate filtered the filtrate was concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography

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

Procedure: A crude peracetic acid solution was prepared by mixing 17.3 g glacial acetic acid (0.29 mole), 7.2 g of a hydrogen peroxide solution having 68% by weight of H2O2 (0.145 mole of H2O2), and 0.7 g concentrated sulphuric acid, and reacting the mixture for several hours at ambient temperature. A solution was obtained which contained 0.10 mole peracetic acid and 0.033 mole uncoverted hydrogen peroxide, and which was introduced into 200 ml of methanol at 0° C. Within the space of half an hour 34.8 g acetone (0.6 mole), 12.2 g of an ammonia solution having 28% by weight NH3 (0.2 mole), and 18.6 g aniline (0.2 mole) were added, after which the mixture was determined by gas phase chromatography to contain 4.6 g of acetone phenylhydrazone (0.031 mole, which was 31% of the theoretical yield compared to the peracid), 1 g of acetone azine (0.009 mole, which was 9% of the theoretical yield), and 0.025 mole of azobenzene. for several hours at ambient temperature A solution was obtained which were added theoretical yield

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

Procedure: A crude peracetic acid solution was prepared by mixing 17.3 g glacial acetic acid (0.29 mole), 7.2 g of a hydrogen peroxide solution having 68% by weight of H2O2 (0.145 mole of H2O2), and 0.7 g concentrated sulphuric acid, and reacting the mixture for several hours at ambient temperature. A solution was obtained which contained 0.10 mole peracetic acid and 0.033 mole uncoverted hydrogen peroxide, and which was introduced into 200 ml of methanol at 0° C. Within the space of half an hour 34.8 g acetone (0.6 mole), 12.2 g of an ammonia solution having 28% by weight NH3 (0.2 mole), and 18.6 g aniline (0.2 mole) were added, after which the mixture was determined by gas phase chromatography to contain 4.6 g of acetone phenylhydrazone (0.031 mole, which was 31% of the theoretical yield compared to the peracid), 1 g of acetone azine (0.009 mole, which was 9% of the theoretical yield), and 0.025 mole of azobenzene. for several hours at ambient temperature A solution was obtained which were added theoretical yield

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetone azine (1.50 g, 13.4 mmol) was dissolved in 10 mL of diethyl ether, mixed with 32 mL (19.2 mmol) of 0.6 M benzylmagnesium bromide in tetrahydrofuran and stirred at 45° C. for 24 hours. The reaction was quenched with saturated aqueous ammonium chloride (100 ml), and the reaction solution was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using hexane-ethyl acetate (9:1 to 6:1) as the eluent to give 710 mg of the desired product as a pale yellow oil. The reaction was quenched with saturated aqueous ammonium chloride (100 ml) the reaction solution was extracted with ethyl acetate The resulting organic layer was dried over anhydrous magnesium sulfate filtered the filtrate was concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography

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

Procedure: Acetone azine (93 g) is added dropwise under reflux to a solution of propylmagnesium bromide, prepared from 44.3 g of magnesium and 224 g of propyl bromide in 350 ml of ether. After heating under reflux for 3 days, the mixture is poured into an ice-cooled aqueous ammonium chloride solution (500 ml) and the product is extracted using ether. The ether phase is concentrated, and the oily residue is stirred at room temperature for 2 h in 200 ml of water and 100 ml of conc. hydrochloric acid. The non-basic components are removed using tert-butyl methyl ether and the aqueous solution is concentrated on a rotary evaporator. After heating under reflux for 3 days the product is extracted The ether phase is concentrated The non-basic components are removed the aqueous solution is concentrated on a rotary evaporator

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetone azine (1.50 g, 13.4 mmol) was dissolved in 10 mL of diethyl ether mixed with 32 mL (19.2 mmol) of 0.6 M benzylmagnesium bromide in tetrahydrofuran and stirred at 45° C. for 24 hours. The reaction was quenched with saturated aqueous ammonium chloride (100 ml), and the reaction solution was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using hexane-ethyl acetate (9:1 to 6:1) as the eluent to give 710 mg of the desired product as a pale yellow oil. The reaction was quenched with saturated aqueous ammonium chloride (100 ml) the reaction solution was extracted with ethyl acetate The resulting organic layer was dried over anhydrous magnesium sulfate filtered the filtrate was concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography

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

Procedure: A crude peracetic acid solution was prepared by mixing 17.3 g glacial acetic acid (0.29 mole), 7.2 g of a hydrogen peroxide solution having 68% by weight of H2O2 (0.145 mole of H2O2), and 0.7 g concentrated sulphuric acid, and reacting the mixture for several hours at ambient temperature. A solution was obtained which contained 0.10 mole peracetic acid and 0.033 mole uncoverted hydrogen peroxide, and which was introduced into 200 ml of methanol at 0° C. Within the space of half an hour 34.8 g acetone (0.6 mole), 12.2 g of an ammonia solution having 28% by weight NH3 (0.2 mole), and 18.6 g aniline (0.2 mole) were added, after which the mixture was determined by gas phase chromatography to contain 4.6 g of acetone phenylhydrazone (0.031 mole, which was 31% of the theoretical yield compared to the peracid), 1 g of acetone azine (0.009 mole, which was 9% of the theoretical yield), and 0.025 mole of azobenzene. for several hours at ambient temperature A solution was obtained which were added theoretical yield

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetone azine (1.50 g, 13.4 mmol) was dissolved in 10 mL of diethyl ether, mixed with 32 mL (19.2 mmol) of 0.6 M benzylmagnesium bromide in tetrahydrofuran and stirred at 45° C. for 24 hours. The reaction was quenched with saturated aqueous ammonium chloride (100 ml), and the reaction solution was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using hexane-ethyl acetate (9:1 to 6:1) as the eluent to give 710 mg of the desired product as a pale yellow oil. The reaction was quenched with saturated aqueous ammonium chloride (100 ml) the reaction solution was extracted with ethyl acetate The resulting organic layer was dried over anhydrous magnesium sulfate filtered the filtrate was concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography