Synthetic method of methylsulfonone ketone

A technology of mesotrione and mesotrione, which is applied in organic chemistry methods, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as corrosiveness and unfriendly environment.

Active Publication Date: 2021-12-21
GHARDA CHEM LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reagents routinely used in the synthesis of

Method used

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  • Synthetic method of methylsulfonone ketone
  • Synthetic method of methylsulfonone ketone
  • Synthetic method of methylsulfonone ketone

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preparation example Construction

[0038] According to the present disclosure, the synthesis method of crystalline mesotrione comprises the following steps:

[0039] i. reacting p-toluenesulfinyl chloride with at least one alkali metal sulfite and at least one alkali metal bicarbonate to obtain an alkali metal p-toluenesulfinate, which is combined with reacting at least one alkali metal monochloroacetic acid salt to obtain p-methylsulfonyltoluene;

[0040] ii. nitrating p-methylsulfonyltoluene using a mixture of sulfuric acid and at least one nitrating agent to obtain 2-nitro-p-methylsulfonyltoluene;

[0041] iii. Oxidizing 2-nitro-p-methylsulfonyltoluene using at least one oxidizing agent in the presence of at least one first catalyst to obtain 2-nitro-p-methylsulfonylbenzoic acid;

[0042] iv. Halogenating 2-nitro-p-methylsulfonylbenzoic acid using at least one halogenating agent in a first fluid medium to obtain 2-nitro-p-methylsulfonylbenzoyl halide;

[0043] v. In the presence of a second fluid medium an...

Embodiment approach

[0101] Typically, the base is selected from the group consisting of triethylamine, sodium hydride and 1,2,4-triazole. According to an exemplary embodiment of the present disclosure, the base is triethylamine, and the third fluid medium is 1,2-dichloroethane.

[0102] The material comprising mesotrione is processed using known techniques to obtain mesotrione with a purity of less than or equal to 99%.

[0103] Step Seven: Converting Amorphous Mesotrione to Crystalline Mesotrione

[0104] method 1

[0105] In the first step, the amorphous mesotrione is dissolved using a fourth fluid medium to obtain a solution. In an exemplary embodiment of the present disclosure, the fourth fluid medium is 1,2-dichloroethane.

[0106] In a second step, the solution is treated with charcoal to obtain a first mixture.

[0107] In the third step, a part of the fourth fluid medium is distilled off from the first mixture to obtain a second mixture comprising the remaining part of the fourth ...

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Abstract

The present disclosure relates to methods of synthesis of mesotrione. The process comprises reacting p-toluenesulfinyl chloride with an alkali metal sulfite and an alkali metal bicarbonate to obtain an alkali metal p-toluenesulfinate. Reaction of p-toluene alkali metal sulfinate with monochloroacetic acid alkali metal salt gives p-methylsulfonyltoluene. Furthermore, p-methylsulfonyltoluene is nitrated to obtain 2‑nitrop-methylsulfonyltoluene. Oxidation and halogenation of 2-nitro-p-methylsulfonyltoluene to give 2-nitro-p-methylsulfonylbenzoyl halide. Reaction of 2-nitro-p-methylsulfonylbenzoyl halide with alkali metal salt of 1,3-cyclohexanedione to obtain 3-(2-nitro-p-methylsulfonylbenzoyloxy)cyclohexane- 1-ketone. Reaction of 3-(2-nitro-p-methylsulfonylbenzoyloxy)cyclohexane-1-one with a base, a third fluid medium and a source of cyanide ions to obtain amorphous mesotrione. The present disclosure also discloses a step of converting amorphous mesotrione to crystalline mesotrione having a purity greater than 99%. The preparation method of mesotrione of the present disclosure is rapid, economical and environmentally friendly.

Description

technical field [0001] The present disclosure relates to methods of synthesis of mesotrione. [0002] definition [0003] As used in this disclosure, the following terms generally have the meanings set forth below, unless indicated otherwise by the context in which they are used. [0004] Crystalline Mesotrione: The term "crystalline mesotrione" refers to a thermodynamically stable form of mesotrione. Crystalline mesotrione was characterized by the following 2Θ values: 8.57, 17.11, 17.49, 18.78, 19.09, 19.53, 21.16, 25.74 and 28.69. [0005] Metastable form of mesotrione: The term "metastable form of mesotrione" refers to a thermodynamically unstable form of mesotrione. The metastable form of mesotrione was characterized by the following 2Θ values: 15.93, 16.99, 19.01, 20.55, 23.24 and 28.58. Background technique [0006] 2-[4-(Methylsulfonyl)-2-nitrobenzoyl]cyclohexane-1,3-dione is a second-generation triketone commonly known as "mesotrione". [0007] [0008] Mesot...

Claims

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Application Information

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IPC IPC(8): C07C317/24
CPCC07C315/02C07C315/04C07C317/24C07B2200/13C07C317/14C07C317/44
Inventor K·H·格哈达S·S·马瑟N·J·简恩S·V·萨瑟P·D·达马尼亚
Owner GHARDA CHEM LTD
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