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A kind of preparation method of sulfophenylpyrazolone and its intermediate

A technology of sulfophenylpyrazolone and alkylating reagent, which is applied in the field of organic synthesis, can solve the problems of unsuitability for industrial production, harsh reaction conditions, and high cost of raw materials, so as to avoid the problems of safety and three wastes, high total yield, low cost effect

Active Publication Date: 2018-08-31
ZHEJIANG ZHUJI UNITED CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The raw material cost of this method is high and difficult to obtain, and metal organic reagents are used, the reaction conditions are harsh, and it is not suitable for industrial production

Method used

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  • A kind of preparation method of sulfophenylpyrazolone and its intermediate
  • A kind of preparation method of sulfophenylpyrazolone and its intermediate
  • A kind of preparation method of sulfophenylpyrazolone and its intermediate

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preparation example Construction

[0041] A preparation method of sulfophenylpyrazolone, comprising the steps of:

[0042] Step 1, in a solvent and in the presence of a base, after compound (I) and compound (II) react at a certain temperature, continue to react with an oxidant to obtain compound (III);

[0043] Step 2, after compound (III) reacts with an acid chloride reagent, then reacts with alcohol at a certain temperature to obtain compound (IV), or compound (III) reacts with an alkylating agent at a certain temperature under the action of a base to obtain compound ( IV);

[0044] Step 3, react compound (IV) with sulfide (V) at a certain temperature in a solvent and in the presence of a base to obtain compound (VI);

[0045] Step 4, compound (VI) is hydrolyzed with alkali, then oxidized with hydrogen peroxide to form compound (VII), or oxidized with hydrogen peroxide, and then hydrolyzed with alkali to form compound (VII);

[0046] Step 5, compound (VII) is reacted with an acid chloride reagent to obtain ...

Embodiment 1

[0065] Embodiment 1: the preparation of 4-chloro-3-nitrobenzotrifluoride

[0066] In a 1000mL three-necked flask, add 400g of p-chlorobenzotrifluoride, add dropwise a mixed acid of 273g of 98% sulfuric acid and 190g of 98% nitric acid at 30°C, continue to react for 4 hours after the dropwise addition, separate the organic layer, and wash the organic layer with water Two times, 480g of 4-chloro-3-nitrobenzotrifluoride was obtained, the yield was 96%.

Embodiment 2

[0067] Embodiment 2: Preparation of 2-nitro-4-trifluoromethylbenzoic acid

[0068] In a 1000mL three-necked flask, add 500g DMF, 180g potassium carbonate, 78g ethyl cyanoacetate and 150g 4-chloro-3-nitrobenzotrifluoride, control the temperature of the reactant within 50°C, and stir for 1 hour. Then add 230g 35% H 2 o 2 , reacted for 2 hours, quenched hydrogen peroxide, distilled and recovered DMF, added water, acidified with hydrochloric acid, solid precipitated, filtered, washed the filter cake with water, and dried to obtain 149g of 2-nitro-4-trifluoromethylbenzoic acid. 1 H-NMRδppm (DMSO-d 6 ) 14.39 (br, 1H), 8.46 (s, 1H), 8.21 (d, J=8.0Hz, 1H), 8.09 (d, J=8.0Hz, 1H).

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Abstract

The invention discloses a preparation method of sulfophenylpyrazolone. The method uses compound (I) as a raw material, carries out a substitution reaction with compound (II) in the presence of a base, and then undergoes oxidation with an oxidant to prepare compound (III), compound (III) is esterified to obtain compound (IV), compound ( IV) Compound (VI) is obtained by thioreaction, compound (VI) is then oxidized, hydrolyzed (or hydrolyzed, oxidized) to obtain compound (VII), and compound (VII) is subjected to acid chloride to obtain acid chloride (VIII) and 1 , 3-dimethyl-5-hydroxypyrazole undergoes an esterification reaction to obtain compound (IX), and finally compound (IX) is rearranged to obtain compound (X). The beneficial effects of the invention are mainly reflected in the following: the raw materials are cheap and easy to obtain, the reaction conversion rate is high, the three wastes are few, and the industrial production is favorable.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of sulfophenylpyrazolone and an intermediate thereof. Background technique [0002] Sulphophenylpyrazolone is an important class of organic compounds, which are widely used in the fields of medicine and pesticides. For example, sulfoxapyrazole is a new type of benzoylpyrazole herbicide developed by Bayer in 1999 and launched in the United States, Canada and Australia in 2008. The herbicide has a wide herbicidal spectrum, can well solve the problem of resistant weeds in wheat fields, has high safety, and has wide application value and market prospect. [0003] At present, the method for preparing pyrazole sulfonyl uses 4-trifluoromethyl-2-thiamphenicol as raw material, through acid chlorination, the acid chloride obtained is then combined with 1,3-dimethyl-5-hydroxypyridine Azole or pyrazolone can be obtained by base-catalyzed reaction (US4261729...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/20C07C309/77C07C303/26
Inventor 苏叶华周君津梁小明滕海鸽张盼蔡国平虞小华陈邦池
Owner ZHEJIANG ZHUJI UNITED CHEM
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