Preparation method of diamido nitrogen-containing aromatic heterocycle compound
A technology for aromatic heterocycles and compounds, which is applied in the field of preparation of diaminonitrogen-containing aromatic heterocycles, can solve problems such as unfavorable yields, and achieve the effects of simple and environmentally friendly routes, low cost, and mild reaction conditions
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[0067] The invention provides a kind of preparation method of diamino nitrogen-containing aromatic heterocyclic compound, comprising the following steps:
[0068] A) mixing a compound having a structure shown in formula (I), water and an inorganic acid, and reacting to obtain a first mixed solution;
[0069] o 2 N-R-NO 2 (I);
[0070] Wherein, R is a group including a nitrogen-containing aromatic heterocyclic ring structure;
[0071] B) mixing the first mixed solution with a sulfide, and reacting to obtain a second mixed solution;
[0072] C) mixing the second mixed solution with lye, and reacting to obtain a diamino nitrogen-containing aromatic heterocyclic compound having a structure shown in formula (II);
[0073] h 2 N-R-NH 2 (II);
[0074] Wherein, R is a group including a nitrogen-containing aromatic heterocyclic ring structure.
[0075] In the present invention, the compound having the structure shown in formula (I) is mixed with an inorganic acid to obtain a ...
Embodiment 1
[0080] Among the compounds having the structure shown in formula (I), R has the structure shown in formula (1), to obtain 2-(4-nitrophenyl)-5-nitrobenzimidazole.
[0081] At room temperature, 2-(4-nitrophenyl)-5-nitrobenzimidazole (2.84 g, 0.01 mol) and 50 mL of water were added to a 100 mL single-necked flask, and phosphoric acid was added dropwise to adjust the pH value below 1. Solid sodium sulfide (3.9 g, 0.05 mol) was added, the temperature was raised to 100° C., and the reaction was continued for 12 h. After cooling down to room temperature, filter, add concentration in the filtrate and be 25wt% sodium carbonate aqueous solution to be neutralized to pH value 7, product precipitates out from reaction system, filter, wash with water several times, dry, obtain 2.15g product 2-(4 -Aminobenzene)-5-aminobenzimidazole (yield 96%, purity (HPLC)>99.9%), 1H-NMRδ (300MHz, DMSO-d6): 11.52 (s, 1H), 8.08 (d, 2H) , 7.47 (d, 1H), 7.10 (d, 1H), 6.62 (m, 3H), 5.30 (s, 2H), 5.18 (s, 2H) p...
Embodiment 2
[0083] Among the compounds having the structure shown in formula (I), R has the structure shown in formula (2), to obtain 2-(4-nitrophenyl)-5-nitrobenzoxazole.
[0084] At room temperature, add 2-(4-nitrophenyl)-5-nitrobenzoxazole (3.22g, 0.01mol) and 50mL water into a 100mL one-necked flask, add phosphoric acid dropwise, and adjust the pH value below 1 . Solid sodium thiosulfite (8.5g, 0.06mol) was added, the temperature was raised to 100°C, and the reaction continued for 16h. After cooling down to room temperature, filter, add concentration in the filtrate and be 25wt% sodium carbonate aqueous solution to neutralize to pH value 7, product precipitates out from reaction system, filter, wash with water several times, dry, obtain 2.14g product 2-(4 -Aminophenyl)-5-aminobenzoxazole (yield 95%, purity (HPLC)>99.9%), 1H-NMRδ (300MHz, DMSO-d6): 7.81 (m, 3H), 6.90 (d, 1H), 6.74 (m, 3H), 6.62 (m, 3H), 5.28 (s, 2H), 5.10 (s, 2H) ppm.
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