Process for producing 1-sbustituted 3, 5-diaminobenzene
A technology of diaminobenzene and radicals, which is applied to the preparation of aminohydroxyl compounds, chemical instruments and methods, and the preparation of organic compounds, and can solve the problems of a large number of manufacturing processes and high manufacturing costs
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Embodiment 1
[0250] In a 1L eggplant flask, weigh 63g (0.5mol) of 1,3,5-trihydroxybenzene and 291g (3mol) of diallylamine, then add 52g (0.5mol) of sodium bisulfite (NaHSO 3 ). The mixture was heated to diallylamine reflux (140-150° C.) while stirring under a light-shielding, solvent-free, and nitrogen atmosphere, and then reacted under heating for 12 hours. After the reaction was completed and cooled to 40°C, 250 ml of toluene was added to the reaction mixture, stirred, and the soluble part (solution part) and insoluble part (sediment) were separated by pipetting, and the solution was taken out. Add 50mL of toluene to the above-mentioned heap for extraction, and combine the extract with the solution taken out earlier. Next, while heating this solution, toluene and unreacted diallylamine were distilled off under reduced pressure, and the resulting residue was washed with distilled water.
[0251] 200 mL of toluene was added to the above-mentioned toluene-extracted heap to dissolve, and t...
Embodiment 2
[0258] [Synthesis of the compound represented by the above formula (3)]
[0259] Compound (3-1) was synthesized according to the following Synthetic Scheme 1-1.
[0260]
[0261] Synthetic route 1-1
[0262] (In Synthetic Route 1-1, Rs is p-chlorobenzenesulfonyl).
[0263] In a 300mL three-necked flask, add 14.2g (50.0mmol) of the compound (1-1) obtained in Example 1 above, 22.02g (250mmol) of ethylene carbonate, 1.61g of tetrabutylammonium bromide and 100g of N, N-dimethylformamide was stirred at 150°C for 2.5 hours to react. After the reaction was completed, 200 mL of ethyl acetate and 50 mL of methanol were added to the reaction mixture to mix, and all the mixture was transferred to a separatory funnel, and the organic layer was washed successively by 10% by weight of sodium hydroxide aqueous solution and distilled water. Thereafter, the solvent was removed under reduced pressure to obtain 14.8 g of compound (3-1).
[0264] Determination of the compound (3-1) 1 In...
Embodiment 3
[0286] [Compound R 1 -Synthesis of COOH]
[0287] According to the following synthetic route 2-1, synthetic compound (R 1 -OH-1).
[0288]
[0289] Synthetic route 2-1
[0290] In 40 mL of ethyl acetate, 7.77 g (20 mmol) of β-cholestanol, 4.0 g (40 mmol) of succinic anhydride and 0.29 g (2.4 mmol) of dimethylaminopyridine were mixed. After adding 3.3 mL (24 mmol) of triethylamine there, it stirred at 95 degreeC for 5 hours, and it reacted. After completion of the reaction, the solvent was replaced with chloroform, followed by washing with 10% by weight hydrochloric acid and distilled water in this order. Afterwards, the solvent was removed under reduced pressure, and the obtained solid was thoroughly washed with ethyl acetate, and the ethyl acetate was removed under reduced pressure to obtain 4.67 g (9.56 mmol) of compound (R 1 -COOH-1) (yield 47.8%).
[0291] Determination of the compound (R 1 -COOH-1) 1 In H-NMR, the chemical shifts are shown below.
[0292] 1...
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