Preparation method of meconazole intermediate

A technology of myclofluzoconazole and intermediates, which is applied in the field of intermediate compound preparation, can solve the problems of harsh conditions, harsh production environment, large amount of three wastes, etc., so as to avoid harsh reaction conditions, improve yield and purity, and reduce production cost effect

Pending Publication Date: 2022-05-10
PAPANNA BEIJING TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Aiming at the defects existing in the existing synthesis process of flufeconazole intermediates, the present invention proposes a synthesis route of "carbonyl protection-etherification-hydrolysis (decarbonylation)", which not only omits the Grignard reaction, but also has milder reaction conditions in the new process , and the waste water is less and easy to handle, it is more suitable for large-scale industrial production, and solves the problems of harsh conditions, large amount of three wastes, and harsh production environment in the existing intermediate synthesis line

Method used

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  • Preparation method of meconazole intermediate
  • Preparation method of meconazole intermediate
  • Preparation method of meconazole intermediate

Examples

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Embodiment 1

[0045] Preparation of 4-(4-chlorophenoxy)-2-trifluoromethylacetophenone

[0046] Step 1: in the four-neck flask that mechanical stirring, thermometer, condenser are housed, add 23.7g (0.1mol, 98%) 4-nitro-2-trifluoromethyl acetophenone (formula (I)) and 150mL solvent xylene, then add 11.2g (0.12mol, 99%) aniline and 5.0g (0.05mol, 98%) sulfuric acid (catalyst), heat up and reflux and stir for 6h, and continuously distill out the water produced by the reaction, then cool down, Then add washing alkali to neutralize and separate the layers, and the organic layer (containing the intermediate product A formula (II)) directly goes to the next step for reaction. After measurement, the reaction yield was 94%.

[0047] Step 2: In the four-neck flask equipped with mechanical stirring, thermometer, and condenser tube, add the above-mentioned reaction product intermediate layer (intermediate product A) and 200ml DMF (solvent), then add 12.9g (0.1mol, 99%) p-chlorine Phenol (reactant) an...

Embodiment 2

[0051] The difference from Example 1 is that in step 1: the protected raw material aniline is replaced by benzylamine, sulfuric acid is replaced by p-toluenesulfonic acid, and other conditions remain unchanged, the content of the target product formula (I) is finally obtained 98%, and the yield is 89% .

Embodiment 3

[0053] Different from Example 1, in step 1: the carbonyl protection reaction is carried out under alkaline conditions, and the protection raw material aniline is replaced by hydroxylamine hydrochloride, sulfuric acid is replaced by sodium acetate, and other conditions are unchanged, and finally the target product formula ( I) content 97%, yield 80%.

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Abstract

The invention belongs to the technical field of preparation of intermediate compounds, and particularly relates to a preparation method of a meconazole intermediate. According to the preparation method of the meconazole intermediate, 4-nitro-2-trifluoromethyl acetophenone is taken as a raw material, and a target product is synthesized through a carbonyl protection reaction, an etherification reaction and a hydrolysis reaction (decarbonylation). The method disclosed by the invention is milder in reaction condition, less in wastewater and easy to treat, is more suitable for industrial large-scale production, and solves the problems of harsh conditions, large amount of three wastes, severe production environment and the like in the existing intermediate synthesis route. Moreover, 4-nitro-2-trifluoromethyl acetophenone is used as a raw material, so that the method is not only suitable for a new synthesis process, but also greatly reduces the cost of raw materials for synthesizing the meconazole intermediate, and has more practical economic benefits.

Description

technical field [0001] The invention belongs to the technical field of preparation of intermediate compounds, and in particular relates to a method for preparing an intermediate of fluflufeconazole. Background technique [0002] Mefentrifluconazole (common name: Mefentrifluconazole) is an epoch-making triazole fungicide newly developed by BASF, which was officially launched in 2019. It has broad-spectrum, high-efficiency, systemic, eradicating and protective effects, especially has outstanding biological activity against a variety of fungal diseases that are difficult to control, and can significantly strengthen the control of more than 60 crop diseases, such as corn, grains, soybeans, etc. Field crops, as well as economic crops such as green peppers and grapes, can also be used for lawn and seed treatment, etc. It not only has higher biological activity, but also has good environmental characteristics, low toxicity to mammals, bees, etc., and high safety. [0003] 4-(4-Ch...

Claims

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Application Information

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Patent Type & AuthorityApplications(China)
IPC IPC(8): C07C45/42C07C49/84
CPCC07C45/42C07C249/02C07C49/84C07C251/24
Inventor焦体谭徐林李生学李星强
OwnerPAPANNA BEIJING TECH