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A kind of preparation method of high-purity 1h-1,2,3-triazole
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A 1H-1 and triazole technology, applied in organic chemistry and other fields, can solve the problems of poor product stability, large production energy consumption, low decarboxylation yield, etc., and achieve good stability, reduce production costs, and high purity.
Active Publication Date: 2019-01-25
SHANGHAI JINJING CHEM CO LTD
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This preparation method uses copper powder or copper oxide as a catalyst with poor reaction selectivity and poor purity, so the product stability is also poor, and the yield of oxidation and high-temperature dry distillation decarboxylation is low, the energy consumption of large-scale production is high, and the production capacity is small, so the production cost is low. high
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Embodiment 1
[0031] Preparation of compound (b) 1H-1,2,3-triazole-4,5-dicarboxylic acid:
[0032] Add 3600L of water to a 6000L stainless steel reaction kettle, then add 400 kg of benzotriazole, 380 kg of caustic soda, heat up to 40°C, then slowly add 2800 kg of potassium permanganate for about 2.0 hours, and control the temperature at 40-80°C, add and keep warm for 2 hours, TLC to follow the reaction, filter to remove manganese dioxide after the reaction is completed, the solution is faded with 30-50% hydrogen peroxide, remove residual manganese dioxide, and the filtrate is cooled to 35°C, adjusted with concentrated hydrochloric acid PH 2.5, then cooled to 5°C to crystallize for 2.0 hours, centrifuged to dry, washed the filter cake with a small amount of water, and vacuum dried at 70°C for 5.0 hours to obtain 506.6 kg of material, HPLC 99.5%, molar yield 96.0%.
[0033] Preparation of compound (c) 1H-1,2,3-triazole:
[0034] In a 5000L glass-lined reactor, add 3800L of N,N-dimethylformam...
Embodiment 2
[0036] Preparation of compound (b) 1H-1,2,3-triazole-4,5-dicarboxylic acid:
[0037] Add the mother liquor of Example 1 into a 6000L stainless steel reaction kettle, adjust the pH at 6-7 with 30% lye, then add 400 kg of benzotriazole and 300 kg of potassium hydroxide, raise the temperature to 45°C, and then slowly add 2800 kilograms of potassium permanganate, about 3.0-4.0h, temperature control at 40-80°C, heat preservation for 4h after adding, TLC tracking the completion of the reaction, filter to remove manganese dioxide, the solution is faded with 30-50% hydrogen peroxide, remove residual di Manganese oxide, the filtrate was cooled to 30°C, adjusted to pH 1.5 with 40% sulfuric acid, then cooled to 0°C to crystallize for 2.0 hours, filtered, washed with a small amount of water, and dried at 80°C for 4.0 hours to obtain 509.3 kg of material, HPLC99.2%, molar yield is 96.2%.
[0038] Preparation of compound (c) 1H-1,2,3-triazole:
[0039] In a 5000L glass-lined reactor, add ...
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Abstract
The invention relates to a preparation method of high-purity 1H-1,2,3-triazole. The preparation method comprises steps as follows: step (1), benzotriazole is taken as a raw material, potassium permanganate is taken as an oxidizing agent, water is taken as a solvent, and high-purity 1H-1,2,3-triazole-4,5-dicarboxylic acid is obtained through an oxidation ring-opening reaction, purification and drying under the alkaline condition; step (2), 1H-1,2,3-triazole-4,5-dicarboxylic acid obtained in the step (1) has a decarboxylic reaction in an N,N-dimethylformamide solvent under the catalytic action of a catalyst, a target product, namely, high-purity 1H-1,2,3-triazole is obtained through purification, and the catalyst is quinolone, pyridine or a mixture of quinolone and pyridine. In the step (2), quinolone or pyridine is taken as a catalyst to replace conventional copper powder or oxide of copper, the reaction selectivity is good, the yield is high, the product purity is high, and the stability is better.
Description
technical field [0001] The invention belongs to the technical field of fine chemical preparation, and in particular relates to a preparation method of high-purity 1H-1,2,3-triazole. Background technique [0002] 1H-1,2,3-triazole is an important intermediate of the β-lactamase inhibitor tazobactam, and can also be used in the synthesis of other drugs. In addition, high-purity 1H-1,2,3-triazole Azole is also used in cleaning agents for electronic products. [0003] At present, there are mainly four known synthetic methods of 1H-1,2,3-triazole: [0004] (1) For example, in JP0641092, glyoxal, monooxime hydrazone or oxime amide hydrazone are synthesized as intermediates; [0005] (2) As in JP05140121, the sulfonyl hydrazone or acyl hydrazone generated by the reaction of p-toluenesulfonyl hydrazide and 2,2-dichloroacetaldehyde is used as an intermediate to synthesize; [0006] (3) Such as Catino A.1.2.3-Triazole [J]. Ann.chim (Rome) 1968 58 1507-1509. Prepared directly from t...
Claims
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