1-chlorododecane

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-propylol-N'-lauryl ethylenediamine is prepared by dissolving 2 kmol ethylenediamine in 500 liters absolute ethanol and then, while constantly stirring, 2 kmol laurylchloride is added while the temperature is maintained not to exceed 100°C and then the reaction mixture is held for 1.5 hours at that temperature. N'-lauryl-ethylenediamine is formed. Subsequently the reaction mixture is cooled to 30°C, the chloride is precipitated with ammonia and the precipitate is filtered off. The pH value of the pure solution is adjusted to 8.5 and 2 kmol propionaldehyde ia added. The temperature is maintained at 40°C during a subsequent 3 hour period while stirring. Then the alcohol is driven off under vacuum and the unreacted products are washed out with water. The end product has a molecular weight of about 300 and the formula ##EQU12## is maintained not to exceed 100°C

反応条件: temp:165.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a reactor system in accordance with FIG. 1 there were pumped jointly per hour 1.65 kg lauryl alcohol (purity: 97%) and 0.41 kg phosphorus trichloride. The cooling was performed in reaction zone 1 in such a way that the outlet temperature was about 110° C. The residence time in reaction zone 1 was 5 minutes. Following preheating to 150° C for 2.5 minutes, the reaction mixture reached reaction zone 2 in which the reaction temperature was maintained with superheated steam at 165° C. The residence time in reaction zone 2 was 26 minutes. By means of a pressure maintenance valve, the entire reactor system was under a pressure of 30 atm. The product obtained in this manner separated out immediately into two phases. One obtained per hour 1.8 kg of the organic phase corresponding to a yield of 97.5% of lauryl chloride with respect to lauryl alcohol. The purity amounted to 95 weight-percent of lauryl chloride. The product contained 0.14 weight-percent of dilauryl ether. Space-time yield: 1.4 kg/hour, liter. Into a reactor system in accordance with FIG. 1 there were pumped jointly per hour The cooling was performed in reaction zone 1 in such a way that the outlet temperature was about 110° C The residence time in reaction zone 1 Following preheating to 150° C for 2.5 minutes reaction zone 2 in which the reaction temperature The residence time in reaction zone 2 was 26 minutes By means of a pressure maintenance valve, the entire reactor system was under a pressure of 30 atm The product obtained in this manner separated out immediately into two phases

反応条件: temp:165.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a reactor system in accordance with FIG. 1 there were pumped jointly per hour 1.65 kg lauryl alcohol (purity: 97%) and 0.41 kg phosphorus trichloride. The cooling was performed in reaction zone 1 in such a way that the outlet temperature was about 110° C. The residence time in reaction zone 1 was 5 minutes. Following preheating to 150° C for 2.5 minutes, the reaction mixture reached reaction zone 2 in which the reaction temperature was maintained with superheated steam at 165° C. The residence time in reaction zone 2 was 26 minutes. By means of a pressure maintenance valve, the entire reactor system was under a pressure of 30 atm. The product obtained in this manner separated out immediately into two phases. One obtained per hour 1.8 kg of the organic phase corresponding to a yield of 97.5% of lauryl chloride with respect to lauryl alcohol. The purity amounted to 95 weight-percent of lauryl chloride. The product contained 0.14 weight-percent of dilauryl ether. Space-time yield: 1.4 kg/hour, liter. Into a reactor system in accordance with FIG. 1 there were pumped jointly per hour The cooling was performed in reaction zone 1 in such a way that the outlet temperature was about 110° C The residence time in reaction zone 1 Following preheating to 150° C for 2.5 minutes reaction zone 2 in which the reaction temperature The residence time in reaction zone 2 was 26 minutes By means of a pressure maintenance valve, the entire reactor system was under a pressure of 30 atm The product obtained in this manner separated out immediately into two phases

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2.14 g of the product of Step C of Example 1 were dissolved in a mixture containing 1.4 ml of triethylamine and 25 ml of tetrahydrofuran. 1.5 ml of lauryl chloride were added dropwise and after stirring for 30 minutes, the precipitate was filtered off. The filtrate was concentrated to dryness and the residue was taken up in methylene chloride, washed with water and dried. The solvent was eliminated under reduced pressure at 50° C. to obtain 3.2 g of the expected product. the precipitate was filtered off The filtrate was concentrated to dryness washed with water dried was eliminated under reduced pressure at 50° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2.14 g of the product of Step C of Example 1 were dissolved in a mixture containing 1.4 ml of triethylamine and 25 ml of tetrahydrofuran. 1.5 ml of lauryl chloride were added dropwise and after stirring for 30 minutes, the precipitate was filtered off. The filtrate was concentrated to dryness and the residue was taken up in methylene chloride, washed with water and dried. The solvent was eliminated under reduced pressure at 50° C. to obtain 3.2 g of the expected product. the precipitate was filtered off The filtrate was concentrated to dryness washed with water dried was eliminated under reduced pressure at 50° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In accordance with the procedure of Example 10, 72.2 g of 3-dimethylamino-1-propanol and 153.1 g of lauryl chloride are reacted in altogether 250 ml of CHCl3. The reaction mixture is neutralised with 147 ml of 20% NaOH. Yield: 157.2 g (82.1%) of product with a boiling point of 110° C./0.1 torr.

反応条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4.08 g (30 millimoles (mmol)) of 4,5-dimethyl-benzene-1,2-diamine (hereinafter compound “1”) and 2.04 grams (g) (10 mmol) of 1-chloro-dodecane in 20 milliliters (mL) of triethylamine was stirred at 130° C. for 6 hrs under argon. After cooling and addition of dichloromethane (100 mL), the organic solution was washed with aqueous Na2CO3 solution (10%, 40 mL). The aqueous layer was extracted twice with dichloromethane (2×100 mL). The combined organic extracts were dried over MgSO4 and rotary evaporated to dryness. The thin-layer chromatography retention factor (Rf) of the target compound (2) was 0.55 with dichloromethane (MC):methanol (MeOH) (95:5) mixture. Compound (2) was purified by flash chromatography on silica gel in MC:MeOH (95:5) to produce 1.8 g of reddish crystals (60% yield); mp 53-54° C.; 1H NMR (400 MHz, CDCl3) δ 6.56 (1H, s), 6.50 (1H, s), 3.20 (3H, broad s), 3.1 (2H, t, J=8 Hz), 2.26 (3H, s), 2.21 (3H, s), 1.68 (2H, q, J=7 Hz), 1.46 (2H, m), 1.34 (16H, s), 0.92 (3H, t, J=8 Hz); 13C NMR (100 MHz, CDCl3) δ 136.0, 131.8, 128.1, 125.9, 118.4, 113.93, 44.7, 31.9, 29.9, 29.69, 29.65, 29.5, 29.4; Anal. Calcd. for C20H36N2 (MW=304.51): C, 78.88; H, 11.92; N, 9.20. Found: C, 78.95; H, 12.16; N, 9.32. After cooling the organic solution was washed with aqueous Na2CO3 solution (10%, 40 mL) The aqueous layer was extracted twice with dichloromethane (2×100 mL) The combined organic extracts were dried over MgSO4 rotary evaporated to dryness Compound (2) was purified by flash chromatography on silica gel in MC

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In accordance with the procedure of Example 10, 72.2 g of 3-dimethylamino-1-propanol and 153.1 g of lauryl chloride are reacted in altogether 250 ml of CHCl3. The reaction mixture is neutralised with 147 ml of 20% NaOH. Yield: 157.2 g (82.1%) of product with a boiling point of 110° C./0.1 torr.

反応条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4.08 g (30 millimoles (mmol)) of 4,5-dimethyl-benzene-1,2-diamine (hereinafter compound “1”) and 2.04 grams (g) (10 mmol) of 1-chloro-dodecane in 20 milliliters (mL) of triethylamine was stirred at 130° C. for 6 hrs under argon. After cooling and addition of dichloromethane (100 mL), the organic solution was washed with aqueous Na2CO3 solution (10%, 40 mL). The aqueous layer was extracted twice with dichloromethane (2×100 mL). The combined organic extracts were dried over MgSO4 and rotary evaporated to dryness. The thin-layer chromatography retention factor (Rf) of the target compound (2) was 0.55 with dichloromethane (MC):methanol (MeOH) (95:5) mixture. Compound (2) was purified by flash chromatography on silica gel in MC:MeOH (95:5) to produce 1.8 g of reddish crystals (60% yield); mp 53-54° C.; 1H NMR (400 MHz, CDCl3) δ 6.56 (1H, s), 6.50 (1H, s), 3.20 (3H, broad s), 3.1 (2H, t, J=8 Hz), 2.26 (3H, s), 2.21 (3H, s), 1.68 (2H, q, J=7 Hz), 1.46 (2H, m), 1.34 (16H, s), 0.92 (3H, t, J=8 Hz); 13C NMR (100 MHz, CDCl3) δ 136.0, 131.8, 128.1, 125.9, 118.4, 113.93, 44.7, 31.9, 29.9, 29.69, 29.65, 29.5, 29.4; Anal. Calcd. for C20H36N2 (MW=304.51): C, 78.88; H, 11.92; N, 9.20. Found: C, 78.95; H, 12.16; N, 9.32. After cooling the organic solution was washed with aqueous Na2CO3 solution (10%, 40 mL) The aqueous layer was extracted twice with dichloromethane (2×100 mL) The combined organic extracts were dried over MgSO4 rotary evaporated to dryness Compound (2) was purified by flash chromatography on silica gel in MC

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-amino-3-pyridinol (0.10 mol), sodium hydroxide (50%) (30 ml), 1-chlorododecane (0.20 mol) and methyl-tri-octylammonium chloride (8 g) in benzene (300 ml) was stirred overnight at 80° C. The reaction mixture was cooled. The organic layer was separated, washed with 2N NaOH, dried (MgSO4), filtered and the solvent was evaporated. The residue was cooled and the resulting precipitate was filtered off, washed with hexane, petroleum ether and dried, yielding 21 g (75%) of 3-(dodecyloxy)-2-pyridinamine (interm. 2). The reaction mixture was cooled The organic layer was separated washed with 2N NaOH dried (MgSO4) filtered the solvent was evaporated The residue was cooled the resulting precipitate was filtered off washed with hexane, petroleum ether dried

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In accordance with the procedure of Example 10, 72.2 g of 3-dimethylamino-1-propanol and 153.1 g of lauryl chloride are reacted in altogether 250 ml of CHCl3. The reaction mixture is neutralised with 147 ml of 20% NaOH. Yield: 157.2 g (82.1%) of product with a boiling point of 110° C./0.01 torr.