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5-substituted aromatic laydrocarbon tetrazole production method

An aromatic hydrocarbon tetrazole and a production method technology, applied in the direction of organic chemistry, etc., can solve the problems of high toxicity of azido acid, low process yield, unsuitable for industrial production, etc., and achieve the effect of easy operation and simple process

Inactive Publication Date: 2005-12-21
NANTONG HUAFENG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The existing 5-position substituted aromatic tetrazole synthesis process is obtained from the reaction and refinement of aromatic hydrocarbon nitrile and azide under the action of solvent and catalyst. Although the yield is high, the azide is highly toxic and unsuitable for industrial production ; Another kind of technique is to react and refine from alkylnitrile and sodium azide under the action of solvent and catalyst, and its technique yield is lower

Method used

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  • 5-substituted aromatic laydrocarbon tetrazole production method
  • 5-substituted aromatic laydrocarbon tetrazole production method
  • 5-substituted aromatic laydrocarbon tetrazole production method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] In the reactor, add 1 mole of benzonitrile and 1.0 mole (or 0.8 mole, 1.5 mole) of sodium azide to benzene (or toluene) 5 times (or 1 time, 10 times) the weight of benzonitrile ), and add catalyst TEBA (or triethylamine, ammonium chloride) that is benzonitrile consumption 0.2~50% (example 0.2%, 10%, 30%, 50%) by weight, in 10 hours (or Gradually add 1.3 moles (or 0.4 moles, 1.8 moles) of concentrated hydrochloric acid (or concentrated sulfuric acid) within 2 hours, 24 hours), and then stir for 2 to 12 hours after the dropwise addition. After the reaction, add water and stir, filter, The crude product was obtained and dried to obtain the product 5-phenyltetrazolium with a yield of 95%.

[0015] Reaction formula:

[0016]

Embodiment 2

[0018] In the reactor, add 1 mole of o-chlorobenzonitrile and 1.0 mole (or 0.8 mole, 1.5 mole) of sodium azide to 5 times (or 1 time, 10 times) the weight of o-chlorobenzonitrile In toluene (or benzene), and add the catalyst triethylamine (or TEBA, ammonium chloride) that is o-chlorobenzonitrile consumption 0.2~50% (example 0.2%, 10%, 30%, 50%) by weight , slowly add 1.8 moles (or 0.4 moles, 1.2 moles) of concentrated hydrochloric acid (or concentrated sulfuric acid) within 24 hours, and then stir for 2 to 12 hours after the dropwise addition. After the reaction, add water and stir, filter to obtain the crude product , and dried to obtain the product 5-o-chlorophenyl tetrazolium with a yield of 92%.

[0019] Reaction formula:

[0020]

Embodiment 3

[0022] aromatic hydrocarbyl nitrile The R group becomes 2-Br, 3-Cl, 3-Br, 3-F, 4-Cl, 4-Br or 4-F, and all the other steps are the same as in Example 1 to obtain the corresponding 5-substituted aromatic hydrocarbon tetra Azole, the yields are all between 90% and 95%.

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Abstract

This invention has disclosed a manufacturing method for 5-substituted aromatic-tetrazole. In existing of the organic solvent and catalyst, arenenitrile reacts with sodium azide to get it. This invention is easy to use, suitable for production for industrialization, craft is simple, the acceptive rate of the products is up to 90-95 percent.

Description

Technical field: [0001] The invention relates to a nitrogen-containing heterocyclic compound and a preparation method thereof. Background technique: [0002] The 5-substituted aromatic tetrazole is widely used in many fields such as medicine, pesticide, and fine chemical industry. They can not only be used as intermediates of cephalosporins and sartan drugs, but also some aromatic tetrazoles can also be used in nylon 66 and other polymers as a foaming agent for chemicals, a wetting agent for glass fiber reinforced polycarbonate, and a solubilizer for mineral oil. [0003] The existing 5-position substituted aromatic tetrazole synthesis process is to react and refine aromatic hydrocarbon nitrile and azide under the action of a solvent and a catalyst. Although the yield is high, the azide has high toxicity and is not suitable for industrial production ; Another technique is to react and refine from alkylnitrile and sodium azide under the action of a solvent and a catalyst, an...

Claims

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Application Information

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IPC IPC(8): C07D257/04
Inventor 王德峰王炳才朱小飞
Owner NANTONG HUAFENG CHEM