1-dodecylpyrrole-2,5-dione

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

実験手順: This compound is prepared by the procedure of Example 1 from 1.20 g (50 mmol) of sodium hydride, 8.21 g (50 mmol) of 2-tert-butyl-6-methylphenol, and 13.27 g (50 mmol) of N-n-dodecylmaleimide in tert-butyl alcohol. The residue is purified by preparative HPLC (8:2 heptane:ethyl acetate eluent) to give 4.70 g (22%) of a yellow wax. The residue is purified by preparative HPLC (8:2 heptane:ethyl acetate eluent) to give 4.70 g (22%) of a yellow wax

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

実験手順: This compound is prepared by the procedure of Example 1 from 1.20 g (50 mmol) of sodium hydride, 8.21 g (50 mmol) of 2-tert-butyl-6-methylphenol, and 13.27 g (50 mmol) of N-n-dodecylmaleimide in tert-butyl alcohol. The residue is purified by preparative HPLC (8:2 heptane:ethyl acetate eluent) to give 4.70 g (22%) of a yellow wax. The residue is purified by preparative HPLC (8:2 heptane:ethyl acetate eluent) to give 4.70 g (22%) of a yellow wax

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

実験手順: This compound is prepared by the procedure of Example 1 from 2.40 g (0.1 mol) of sodium hydride, 20.63 g (0.1 mol) of 2,6-di-tert-butylphenol, and 26.54 g (0.1 mol) of N-n-dodecylmaleimide in tert-butyl alcohol. The reaction mixture is concentrated in vacuo and the residue is dissolved in 800 ml of toluene. The toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (6×200 ml). The organic phase is dried over anhydrous sodium sulfate. The solvent is removed in vacuo and the residue purified by flash chromatography (8:2 heptane: ethyl acetate eluent) followed by recrystallization from petroleum ether to give 8.15 g (17%) of a white solid: mp 66°-70° C. The reaction mixture is concentrated in vacuo the residue is dissolved in 800 ml of toluene The toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (6×200 ml) The organic phase is dried over anhydrous sodium sulfate The solvent is removed in vacuo the residue purified by flash chromatography (8:2 heptane: ethyl acetate eluent) followed by recrystallization from petroleum ether

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

実験手順: This compound is prepared by the procedure of Example 1 from 2.40 g (0.1 mol) of sodium hydride, 20.63 g (0.1 mol) of 2,6-di-tert-butylphenol, and 26.54 g (0.1 mol) of N-n-dodecylmaleimide in tert-butyl alcohol. The reaction mixture is concentrated in vacuo and the residue is dissolved in 800 ml of toluene. The toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (6×200 ml). The organic phase is dried over anhydrous sodium sulfate. The solvent is removed in vacuo and the residue purified by flash chromatography (8:2 heptane: ethyl acetate eluent) followed by recrystallization from petroleum ether to give 8.15 g (17%) of a white solid: mp 66°-70° C. The reaction mixture is concentrated in vacuo the residue is dissolved in 800 ml of toluene The toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (6×200 ml) The organic phase is dried over anhydrous sodium sulfate The solvent is removed in vacuo the residue purified by flash chromatography (8:2 heptane: ethyl acetate eluent) followed by recrystallization from petroleum ether

反応条件: temp:210.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The same reactor as used in Example 7 was adopted. In this reactor, a solution of 120 g of maleic anhydride in 360 g of tetrahydronaphthalene was placed. Then, a solution of 220 g of dodecylamine and 1760 g of tetrahydronaphthalene was added thereto at 40° C. over a period of 120 minutes. After the addition was completed, the resultant mixture and 65.4 g of ortho-phosphoric acid (purity 89% by weight), 1.344 g of methoxybenzoquinone, and 0.1 g of zinc acetate added thereto were heated at 210° C. for one hour to effect reaction. Thereafter, the resultant reaction mixture was cooled to 30° C. and separated into a water layer and a tetrahydronaphthalene layer. The tetrahydronaphthalene layer was distilled to expel tetrahydronaphthalene. Consequently, there was obtained 285 g of slightly impure N-dodecyl maleimide. It was found to have purity of 92.3% by weight, indicating the yield thereof to be 83.5 mol % based on dodecylamine. After the addition reaction Thereafter, the resultant reaction mixture was cooled to 30° C. separated into a water layer The tetrahydronaphthalene layer was distilled

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A glass flask having an inner volume of 3 liters was fitted with a theremometer, a stirrer and a water separater. This reactor was charged with 240 g of a xylene solution containing 120 g of maleic anhydride. Then, a solution of 220 g of dodecylamine in 1880 g of xylene was added thereto gradually and piecemeal at 40° C. over a period of 120 minutes. After the addition was completed, the resultant mixture and 65.4 g of ortho-phosphoric acid (purity 89% by weight), 0.672 g of p-methoxyphenol, and 0.05 g of zinc acetate added thereto were heated at 150° C. for four hours to effect reaction. Thereafter, the resultant reaction mixture was cooled to 30° C., washed with 400 ml of water, and separated into a water layer and a xylene layer. The xylene layer was filtered to effect removal of insolubles. The xylene layer now free from insolubles was distilled to expel xylene. Consequently there was obtained 260 g of slightly impure N-dodecyl maleimide. It was found to have purity of 91.2% by weight, indicating the yield thereof to be 75.3 mol % based on dodecylamine. A glass flask having an inner volume of 3 liters was fitted with a theremometer, a stirrer After the addition reaction Thereafter, the resultant reaction mixture was cooled to 30° C. washed with 400 ml of water separated into a water layer The xylene layer was filtered removal of insolubles The xylene layer now free from insolubles was distilled

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A glass flask having an inner volume of 3 liters was fitted with a theremometer, a stirrer and a water separater. This reactor was charged with 240 g of a xylene solution containing 120 g of maleic anhydride. Then, a solution of 220 g of dodecylamine in 1880 g of xylene was added thereto gradually and piecemeal at 40° C. over a period of 120 minutes. After the addition was completed, the resultant mixture and 65.4 g of ortho-phosphoric acid (purity 89% by weight), 0.672 g of p-methoxyphenol, and 0.05 g of zinc acetate added thereto were heated at 150° C. for four hours to effect reaction. Thereafter, the resultant reaction mixture was cooled to 30° C., washed with 400 ml of water, and separated into a water layer and a xylene layer. The xylene layer was filtered to effect removal of insolubles. The xylene layer now free from insolubles was distilled to expel xylene. Consequently there was obtained 260 g of slightly impure N-dodecyl maleimide. It was found to have purity of 91.2% by weight, indicating the yield thereof to be 75.3 mol % based on dodecylamine. A glass flask having an inner volume of 3 liters was fitted with a theremometer, a stirrer After the addition reaction Thereafter, the resultant reaction mixture was cooled to 30° C. washed with 400 ml of water separated into a water layer The xylene layer was filtered removal of insolubles The xylene layer now free from insolubles was distilled

反応条件: temp:215.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A glass flask having an inner volume of 3 liters was fitted with a thermometer, a stirrer, and a water separator. In this reactor, 240 g of a solution containing 120 g of maleic anhydride in xylene was placed. Then, a solution containing 220 g of dodecylamine in 1880 g of xylene was added gradually and piecemeal over a period of 120 minutes at 40° C. to the reactor. After the addition was completed, the mixture in the reactor and 65.4 g of orthophosphoric acid (purity 89% by weight) added thereto were heated at 215° C. for 1 hour under 4.4 kg/cm2. G to effect reaction. The resultant reaction mixture was cooled to 30° C., washed with 400 ml of water, and separated into a water layer and a xylene layer. The xylene layer was separated by filtration to effect removal of insolubles. The xylene layer was distilled to expel xylene. Consequently, there was obtained 258 g of slightly impure N-dodecyl maleimide. This product was found to have purity of 85.3% by weight, indicating the yield to be 69.9 mol % based on dodecylamine. A glass flask having an inner volume of 3 liters was fitted with a thermometer, a stirrer was added gradually and piecemeal over a period of 120 minutes at 40° C. to the reactor After the addition reaction The resultant reaction mixture was cooled to 30° C. washed with 400 ml of water separated into a water layer The xylene layer was separated by filtration removal of insolubles The xylene layer was distilled

反応条件: temp:215.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A glass flask having an inner volume of 3 liters was fitted with a thermometer, a stirrer, and a water separator. In this reactor, 240 g of a solution containing 120 g of maleic anhydride in xylene was placed. Then, a solution containing 220 g of dodecylamine in 1880 g of xylene was added gradually and piecemeal over a period of 120 minutes at 40° C. to the reactor. After the addition was completed, the mixture in the reactor and 65.4 g of orthophosphoric acid (purity 89% by weight) added thereto were heated at 215° C. for 1 hour under 4.4 kg/cm2. G to effect reaction. The resultant reaction mixture was cooled to 30° C., washed with 400 ml of water, and separated into a water layer and a xylene layer. The xylene layer was separated by filtration to effect removal of insolubles. The xylene layer was distilled to expel xylene. Consequently, there was obtained 258 g of slightly impure N-dodecyl maleimide. This product was found to have purity of 85.3% by weight, indicating the yield to be 69.9 mol % based on dodecylamine. A glass flask having an inner volume of 3 liters was fitted with a thermometer, a stirrer was added gradually and piecemeal over a period of 120 minutes at 40° C. to the reactor After the addition reaction The resultant reaction mixture was cooled to 30° C. washed with 400 ml of water separated into a water layer The xylene layer was separated by filtration removal of insolubles The xylene layer was distilled

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

実験手順: This compound is prepared by the procedure of Example 1 from 1.20 g (50 mmol) of sodium hydride, 8.21 g (50 mmol) of 2-tert-butyl-6-methylphenol, and 13.27 g (50 mmol) of N-n-dodecylmaleimide in tert-butyl alcohol. The residue is purified by preparative HPLC (8:2 heptane:ethyl acetate eluent) to give 4.70 g (22%) of a yellow wax. The residue is purified by preparative HPLC (8:2 heptane:ethyl acetate eluent) to give 4.70 g (22%) of a yellow wax

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

実験手順: This compound is prepared by the procedure of Example 1 from 2.40 g (0.1 mol) of sodium hydride, 20.63 g (0.1 mol) of 2,6-di-tert-butylphenol, and 26.54 g (0.1 mol) of N-n-dodecylmaleimide in tert-butyl alcohol. The reaction mixture is concentrated in vacuo and the residue is dissolved in 800 ml of toluene. The toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (6×200 ml). The organic phase is dried over anhydrous sodium sulfate. The solvent is removed in vacuo and the residue purified by flash chromatography (8:2 heptane: ethyl acetate eluent) followed by recrystallization from petroleum ether to give 8.15 g (17%) of a white solid: mp 66°-70° C. The reaction mixture is concentrated in vacuo the residue is dissolved in 800 ml of toluene The toluene solution is extracted sequentially with 1M sodium hydroxide (2×100 ml) and water (6×200 ml) The organic phase is dried over anhydrous sodium sulfate The solvent is removed in vacuo the residue purified by flash chromatography (8:2 heptane: ethyl acetate eluent) followed by recrystallization from petroleum ether

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1 Mole of maleic anhydride and 300 g of dimethylformamide were charged into a 2-liter three-necked flask and stirred to dissolve the maleic anhydride into the dimethylformamide. To the resulting solution were added, with stirring, 1.02 moles of laurylamine over a period of 30 minutes while cooling the flask in a cold water bath. The exothermic reaction occurred simultaneously with the addition of the laurylamine which was, therefore, so carefully done that the temperature of the reaction mixture could be maintained at around 50° C. Immediately after completion of the addition of the laurylamine, the bath temperature was increased to 50° C. at which the stirring was continued for 1 hour. After completion of the amide-formation reaction, 1.6 moles of acetic anhydride, 0.016 mole of nickel acetate and 0.16 mole of triethylamine were added, with stirring, to the reaction mixture. The resulting mixture was heated to 90°-95° C. at which the stirring was continued for 1.5 hours to effect the dehydration reaction. Subsequently, the reaction mixture was cooled to room temperature and poured into ice and water to yield a precipitate. The precipitate was collected by filtration, washed with water, neutralized with sodium carbonate and recrystallized twice from water-containing ethanol (90%) to obtain white crystals of N-laurylmaleimide having a melting point of 56° C. To the resulting solution were added with stirring The exothermic reaction the bath temperature was increased to 50° C. at which the stirring were added with stirring, to the reaction mixture The resulting mixture was heated to 90°-95° C. at which the stirring was continued for 1.5 hours the dehydration reaction Subsequently, the reaction mixture was cooled to room temperature to yield a precipitate The precipitate was collected by filtration washed with water recrystallized twice from water- containing ethanol (90%)