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Method for preparing 5-substituted thiophenyl-benzimidazol-2-N-methoxycarbonyl compound

A -2-N-, methoxycarbonyl technology, applied in the field of preparation of phenylthio-benzimidazole-2-N-methoxycarbonyl compounds, can solve the problem of lack of market competitiveness, high risk, High price and other problems, to achieve the effect of easy procurement and preservation, low price and low toxicity

Inactive Publication Date: 2012-01-04
湖南欧亚药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Method 1 is the method commonly used at present, but a large amount of sodium hydride is used in the synthetic raw materials, which is relatively dangerous, and the raw material N-(methoxycarbonyl) methyl carbaimidate used is relatively expensive and variable; The starting material 5-chloro-2-nitroacetamidobenzene and cyanoamide used in method two are relatively expensive, and do not have a market competitive advantage; the raw material s-methylisothiourea sulfate used in method three is also relatively expensive high
Moreover, these three methods all use the method of catalytic hydrogenation in the reduction of nitro groups, which have certain restrictions on the equipment of the factory.

Method used

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  • Method for preparing 5-substituted thiophenyl-benzimidazol-2-N-methoxycarbonyl compound
  • Method for preparing 5-substituted thiophenyl-benzimidazol-2-N-methoxycarbonyl compound
  • Method for preparing 5-substituted thiophenyl-benzimidazol-2-N-methoxycarbonyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of Compound IA (R=H):

[0034] 220 g of thiophenol (2.0 mol), 358.8 g of anhydrous potassium carbonate (2.6 mol) and 345 g of 5-chloro-2-nitroaniline (2.0 mol) were added to 2500 ml of N,N-dimethylformamide , reflux reaction for 3 hours, concentrated under reduced pressure and evaporated 1800 milliliters of solvent, the residue was poured into 3000 milliliters of ice water, stirred for 45 minutes, filtered, the filter cake was washed with 1000 milliliters of water, and dried to obtain 468.3 grams of off-white powder.

[0035] Yield: 95.18% (calculated as thiophenol).

[0036] Synthesis of Compound IIA (R=H):

[0037] Add 246 grams of compound I (1.0mol) and 146.3 grams of ammonium chloride (2.5mol) into 1000 milliliters of anhydrous methanol, stir, and under ice-salt bath cooling, add 43.8 grams of sodium borohydride (1.15mol) in batches, and the addition is complete , slowly returned to room temperature, stirred and reacted for 2 hours, after the reacti...

Embodiment 2

[0046] Synthesis of Compound IB (R=p-Cl):

[0047] 144.5 grams of 4-chlorothiophenol (1.0mol), 165.6 grams of anhydrous potassium carbonate and 172.5 grams of 5-chloro-2-nitroaniline were added to 1500 milliliters of N, N-dimethylformamide, refluxed for 5 hours, After the reaction was completed, 1000 ml of solvent was evaporated by concentration, and the residue was added to 1600 ml of ice water, stirred for 45 minutes, filtered, and the filter cake was washed with 800 ml of water and dried to obtain 236.8 g of light yellow solid powder.

[0048] Yield: 84.42% (calculated as 4-chlorothiophenol).

[0049] Synthesis of Compound IIB (R=p-Cl):

[0050]Add 280.5 grams of compound IB and 163.8 grams of ammonium chloride (2.8 mol) into 1200 ml of methanol, stir, cool to -5°C, add 47.5 grams of sodium borohydride (1.25 mol) in batches, after the addition is complete, return to room temperature and stir the reaction After 3 hours, after the reaction was over, the reaction solution wa...

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Abstract

The invention discloses a method for preparing a 5-substituted thiophenyl-benzimidazol-2-N-methoxycarbonyl compound. In the method, a compound (I), a compound (II) and a compound (III) are synthesized respectively; and finally, a compound (IV) is synthesized. In the invention, the synthesis route is short, the raw material is cheap and readily available, the yield is high, the pollution is basically prevented, and industrial production can be carried out.

Description

Technical field [0001] The present invention involves a synthesis method of a compound, which specifically involves the preparation method of a 5-replaced phenyl-phenazil-2-n-methyl oxygenic compound. Background technique [0002] Benzolehililillene -based compound (structural type Ⅰ) is a very good type of deworming medicine, and one of the representative compounds is fertilizazazole (compound ⅠA).Fenatezazole is a spectral deworming medicine for human beasts. It has a high degree of deworming activity for animal gastrointestinal width., And small toxicity and large safety range.In recent years, it should be sold in the domestic and foreign veterinary drug markets. [0003] [0004] Ⅰ [0005] [0006] ⅠA [0007] At present, there are not many synthesis methods for reports of this type of compound, mainly in the following three categories: [0008] Method 1: [Deng Xiaolin, China Pharmaceutical Industry Magazine, 1994,25 (3), 107-108] [0009] [0010] Method two: [Robert ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/32
Inventor 林开朝李兴民陶友妮
Owner 湖南欧亚药业有限公司
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