Preparation method for benzimidazolone

A technology of benzimidazolone and hydroxyethyl benzimidazole is applied in the field of preparation of benzimidazolone, can solve problems such as high cost, waste of resources, increase in cost, etc., achieves simplified synthesis process and operation steps, and saves time and cost , the effect of reducing emissions

Inactive Publication Date: 2019-04-09
JIANGSU NOON CROP SCI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This technique adopts potassium permanganate as oxidant, and the cost is high, and in order to improve the yield of this step, the feeding amount of potassium permanganate will be much larger than the theoretical amount, resulting in a further increase in cost and waste of resources. Another relatively large shortcoming is Potassium permanganate is used as an oxidant to cause this step reaction to produce waste water containing more heavy metal ions, which is difficult to treat and seriously pollutes the environment

Method used

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  • Preparation method for benzimidazolone
  • Preparation method for benzimidazolone

Examples

Experimental program
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Effect test

Embodiment 1

[0023] 1. Pass 50g of o-phenylenediamine and a certain amount of HCl solution into the heterogeneous catalytic oxidation reaction device with copper, zinc and zirconium as composite catalysts and alumina as the carrier in proportion, slowly add 42g of lactic acid dropwise, and the reaction ends Afterwards, the pH value was adjusted to obtain 2-α-hydroxyethylbenzimidazole, which was filtered and dried to obtain 67.3 g of the product, with a content of 98.5% and a yield of 94.7%.

[0024] 2. Put 50g of 2-α-hydroxyethylbenzimidazole into acetone and hydrochloric acid and a heterogeneous loading catalytic oxidation reaction device to obtain 49.4g of product 2-acetylbenzimidazole after the reaction, with a content of 98.4% and a yield of 98.5 %.

Embodiment 2

[0026] 1. Put 100g of o-phenylenediamine and a certain amount of HCl solution in a heterogeneous catalytic oxidation reaction device loaded with copper-zirconium composite catalyst and pure silica as a carrier, slowly add 84g of lactic acid dropwise, and adjust the pH value after the reaction 2-α-Hydroxyethylbenzimidazole was filtered and dried to obtain 145.7 g of the product, with a content of 98.1% and a yield of 95.3%.

[0027] 2. Put 140g of 2-α-hydroxyethylbenzimidazole into acetone, hydrochloric acid and heterogeneous loading catalytic oxidation reaction device, after the reaction, 137.2g of product 2-acetylbenzimidazole was obtained, with a content of 98.9%, and a yield of 98.1 %.

Embodiment 3

[0029] 1. Put 20g of o-phenylenediamine and a certain amount of HCl solution in a heterogeneous catalytic oxidation reaction device loaded with copper and zirconium as a composite catalyst and alumina as a carrier, slowly add 16.8g of lactic acid dropwise, and adjust the pH after the reaction 2-α-Hydroxyethylbenzimidazole was obtained, and 28.0 g of the product was obtained after filtration and drying, with a content of 99.0% and a yield of 92.4%.

[0030] 2. Put 28g of 2-α-hydroxyethylbenzimidazole into acetone and hydrochloric acid and a heterogeneous loading catalytic oxidation reaction device, after the reaction, 27.0g of the product 2-acetylbenzimidazole was obtained, with a content of 98.7% and a yield of 96.5 %.

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Abstract

The invention relates to a method of synthesizing a thiabendazole intermediate benzimidazolone cleanly and environment-friendly by means of one or more of catalytic oxidation devices of heterogeneouscopper, zinc, zirconium, cobalt, nickel, platinum and rhodium. The preparation method comprises the following steps: carrying out a condensation reaction on lactic acid and o-phenylenediamine in a hydrochloric acid aqueous solution; adjusting the PH value to obtain 2-alpha-hydroxyethyl benzimidazole; then filtering the 2-alpha-hydroxyethyl benzimidazole and putting into acetone and hydrochloric acid and the heterogeneous loaded catalytic oxidation devices; carrying out oxidization with oxygen-enriched air or direct air oxidization and combining hydrogen peroxide combined oxidization to prepare2-acetyl benzimidazole (benzimidazolone for short). The method optimizes the synthetic route, is mild in reaction condition, low in cost, high in efficiency, environment-friendly and safe, fully solves the severe pollution problem of heavy metal ion-containing waste water of the reaction in an old process, has a very good application prospect and has a relatively high economical benefit.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of benzimidazolone. Background technique [0002] Thiabendazole (thiabendazole) belongs to the class of benzimidazoles, the molecular formula is C 10 h 7 N 3 S, chemical name: α-(4-thiazolyl)-1H-benzimidazole. The mechanism of action is to inhibit fungal mitochondrial respiration and cell proliferation. It has a systemic conduction function, and can conduct to the top when applied to the root, but not to the base. Antibacterial activity is limited to Ascomycetes, Basidiomycetes, and Deuteromycetes, but is inactive against Oomycetes and Zygomycetes. [0003] [0004] 2-Acetylbenzimidazole [0005] At present, the technological scheme of thiabendazole intermediate 2-acetylbenzimidazole is: lactic acid and o-phenylenediamine are condensed in hydrochloric acid aqueous solution, and the pH value is adjusted to obtain 2-α-hydroxyethylbenzimidazol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/12
CPCC07D235/12
Inventor 孟宪锋
Owner JIANGSU NOON CROP SCI CO LTD
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