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New preparation technology of 2-cyan-4-(p-methylphenyl)-5-chloro-1H-imidazole

A p-tolyl, new process technology, applied in the field of new process for the preparation of 2-cyano-4--5-chloro-1H-imidazole, can solve the problems of unsafe process, difficult preparation, high industrialization cost, etc., and achieve reaction The effect of high total yield, strong operability and low production cost

Inactive Publication Date: 2017-09-01
YANCHENEG HUIHUANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The synthesis methods reported in the relevant literature are complex in process, some use expensive reagents, and the industrialization cost is high
Some processes use dangerous chemicals, the production is highly toxic, the production is unsafe, the risk is high, and the production process is difficult to control, etc.
For example, the raw material used in patent CN104292166 is p-tolylglyoxal, which has no commercial purchase source, and the cost of preparing the raw material is high, and the highly toxic reagent selenium dioxide is used, which has safety risks
Another example is the patent CN103936678 which reports that the target compound is obtained by preparing the nitrogen oxide intermediate, and then reacting to obtain the target compound. Since the nitrogen oxide is unstable, friction is prone to explosion, the process is unsafe, and it is difficult to industrialize production
As in the literature Pestic.Sci.2004,29,136-138, the required reagent diethoxyacetimide has no industrial products, and the preparation is difficult, resulting in an increase in industrial production costs
As reported in the literature "Pesticides", 2015,54(5):324-326, the highly toxic oxide selenium dioxide is used in the synthesis process, which has safety risks

Method used

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  • New preparation technology of 2-cyan-4-(p-methylphenyl)-5-chloro-1H-imidazole
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  • New preparation technology of 2-cyan-4-(p-methylphenyl)-5-chloro-1H-imidazole

Examples

Experimental program
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Effect test

Embodiment 1

[0030] The synthesis of embodiment 1 compound (4):

[0031]

[0032] In a 500ml three-necked flask, add 44.7g (0.3mol) of 1-(p-tolyl)-2-aminoethanone, 53.82g (0.39mol) of potassium carbonate, add 200g of acetonitrile, dropwise add 1-methoxy-2, Add 51.12 g (0.36 mol) of 2-dichloroethylimine dropwise for about 1 hour, and react at room temperature for 4 h until the raw materials are completely reacted, add 50 g of water, and precipitate a solid in an ice bath, and obtain 53.2 g of compound (4) by suction filtration, with a purity of 97.4% , yield 72%.

Embodiment 2

[0033] The synthesis of embodiment 2 compound (4):

[0034] In a 500ml three-necked flask, add 44.7g (0.3mol) of 1-(p-tolyl)-2-aminoethanone, 82.8g (0.60mol) of potassium carbonate, add 150g of acetonitrile, dropwise add 1-methoxy-2, 51.12g (0.36mol) of 2-dichloroethylimine, added dropwise for about 2 hours, reacted at 35°C for 3h, until the raw materials were completely reacted, added 50g of water, precipitated a solid in an ice bath, and filtered with suction to obtain 51.3g of compound (4). 96.8%, yield 69%.

Embodiment 3

[0035] The synthesis of embodiment 3 compound (4):

[0036] In a 500ml three-necked flask, add 44.7g (0.3mol) of 1-(p-tolyl)-2-aminoethanone, 50.88g (0.48mol) of sodium carbonate, add 150g of toluene, dropwise add 1-methoxy-2, 76.67g (0.54mol) of 2-dichloroethylimine, added dropwise for about 1 hour, reacted at 50°C for 2h, until the raw materials were completely reacted, added 50g of water, precipitated a solid in an ice bath, and filtered with suction to obtain 42.4g of compound (4). 90%, yield 53%.

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Abstract

The invention discloses a new preparation technology of 2-cyan-4-(p-methylphenyl)-5-chloro-1H-imidazole. The method comprises the following steps: 1-(p-methylphenyl)-2-aminoethanone, which is used as a raw material, undergoes cyclization to obtain 2,2-dichloromethyl-4-(p-methylphenyl)imidazole; 2,2-dichloromethyl-4-(p-methylphenyl)imidazole reacts with hydroxylamine to obtain oxime; dehydration is further carried out to obtain 2-cyan-4-(p-methylphenyl)imidazole; and finally chlorination is carried out to obtain the target compound. The preparation method has the following advantages: sources of the raw material are wide; operation is safe; and the process is smooth. The preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a new preparation process of 2-cyano-4-(p-tolyl)-5-chloro-1H-imidazole. Background technique [0002] Cyazofamid is a new type of low-toxic fungicide developed by Ishihara Co., Ltd. in Japan. It has good protective activity and certain systemic therapeutic activity. It has a long-lasting effect, is resistant to rain erosion, and is safe and convenient to use. The drug is a mitochondrial respiration inhibitor, and its bactericidal mechanism is to inhibit the Qi in cytochrome Bcl in the process of bacteria metabolism, resulting in the death of bacteria. It has effects on all growth stages of oomycetes, and is active against metalaxyl-resistant or sensitive bacteria. Its chemical formula: C 11 h 8 ClN 3 , chemical name: 2-cyano-4-(p-tolyl)-5-chloro-1H-imidazole, English name: 5-chloro-4-(p-tolyl)-1H-imidazole-2-carbonitrile. The structural formula is as follows: [...

Claims

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Application Information

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IPC IPC(8): C07D233/90
CPCC07D233/90
Inventor 余强董建生郭建法王正荣
Owner YANCHENEG HUIHUANG CHEM