Method for preparing tembotrions

A technology of cyclosulfonone and cyclohexanedione is applied in the field of preparation of cyclosulfonone, can solve the problems of low yield of cyclosulfonone, contains highly toxic substances, and high cost, and achieves high reaction yield, easy operation, and high cost. low effect

Inactive Publication Date: 2016-10-12
HEFEI JIUYI AGRI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to overcome the deficiencies of the prior art and provide a preparation method for tembotrione to s

Method used

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  • Method for preparing tembotrions
  • Method for preparing tembotrions
  • Method for preparing tembotrions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A kind of preparation method of tembotrione provided by the present embodiment comprises the following steps:

[0025] Step a: get 1.1mol (134.2g) sodium trifluoroethoxide, 1.2mol (48g) sodium hydroxide, 1.0mol (318g) 2-chloro-3-bromomethyl-4-methylsulfonylbenzoate (compound 1), 1000mL of N,N-dimethylformamide was added to the reactor, and after 5 hours of heat preservation at 30°C, after the N,N-dimethylformamide in the reaction liquid was evaporated under reduced pressure, the raffinate was Add 300mL of water, adjust the pH to weak acidity with 35% hydrochloric acid, cool and crystallize, filter, wash with water, and dry to obtain compound II, weighing 314.8g, yield 91%, wherein, N,N-Dimethylformamide was used as Reaction solvent can also be used in hexane, cyclohexane, benzene, toluene, xylene, methylene chloride, 1,2-dichloroethane, chloroform, 1,4-dioxane, ether, tetrahydrofuran, acetonitrile one or more alternatives.

[0026] Step b: Take 1 mol of compound II ob...

Embodiment 2

[0028] Another preparation method of tembotrione provided in this embodiment comprises the following steps:

[0029] Step a: get 1.2mol (146.4g) sodium trifluoroethoxide, 1.2mol (67.2g) potassium hydroxide, 1.0mol (318g) 2-chloro-3-bromomethyl-4-methylsulfobenzoic acid methyl ester ( Compound I), 1000mL N,N-dimethylformamide was added to the reactor, and then reacted at 0°C for 10 hours, and the N,N-dimethylformamide in the reaction solution was distilled off under reduced pressure, and then The residual liquid was added to 300 mL of water, and the pH was adjusted to weak acidity with 35% hydrochloric acid, cooled to crystallize, filtered, washed with water, and dried to obtain Compound II, which was weighed to obtain 321.7 g, with a yield of 93%.

[0030] Step b: Take 1 mol of compound II obtained from the above reaction, dissolve it in 1000 mL of dichloromethane, and then add 1.3 mol (145.6 g) of 1,3-cyclohexanedione at a temperature of 8-15°C within half an hour (Compound ...

Embodiment 3

[0032] Another preparation method of tembotrione provided in this embodiment comprises the following steps:

[0033] Step a: get 1.1mol (134.2g) sodium trifluoroethoxide, 1.2mol (129.6g) sodium carbonate, 1.0mol (318g) 2-chloro-3-bromomethyl-4-methylsulfobenzoate (compound 1), 1000mL of N,N-dimethylformamide was added to the reactor, and after 2 hours of heat preservation at 50°C, after the N,N-dimethylformamide in the reaction liquid was evaporated under reduced pressure, the raffinate was Add 300mL of water, adjust the pH to weak acidity with 35% hydrochloric acid, cool and crystallize, filter, wash with water, and dry to obtain compound II, which weighs 311.4g, yield 90%.

[0034] Step b: Take 1 mol of the compound II obtained from the above reaction, dissolve it in 1000 mL of dichloroethane, and then add 1.5 mol (147 g) of 1,3-cyclohexanedione at a temperature of 15-20 ° C within half an hour (Compound III) and 3mol (405g) condensing agent HOBT and 3mol (222g) calcium hyd...

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Abstract

The invention discloses a method for preparing tembotrions, and belongs to the technical field of organic chemical industry. The method comprises the steps that sodium 2,2,2-trifluoroethanolate and 2-chloro-3-brooethyl-4-methylsulfonylpropyl methyl benzoate react, and generated 2-chloro-3-trifluoro-ethoxy methyl-4-methyl sulfone chloride benzoic acid and 1,3-cyclohexanedione are condensed and rearranged to prepare tembotrions. According to the method for preparing tembotrions, the defects that in a traditional method, 2-chloro-3-brooethyl-4-methyl sulfone chloride methyl benzoate, trifluoroethanol and potassium tert-butoxide are used for preparing 2-chloro-3-trifluoro-ethoxy methyl-4-methyl sulfone chloride benzoic acid, the yield is low, and a potassium tert-butoxide reagent is expensive are overcome, meanwhile, the defect that after carboxyl is acylate chlorinated into ester, a toxic catalyst acetone cyanohydrins is needed in a rearrangement method is overcome, the advantages of being high in yield, low in cost, easy to operate, low in pollution, safe, environmentally friendly and the like are achieved, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of organic chemical industry, in particular to a preparation method of tembotrione. Background technique [0002] Tebutrione is a class of herbicides with high activity, low dosage and relatively safe so far. Its industrial preparation method is mainly trifluoroethanol and potassium tert-butoxide method to prepare the key intermediate 2-chloro-3-trifluoro Ethoxymethyl-4-methanesulfobenzoic acid is then rearranged after carboxylic acid chloride to form an ester, and the yield of the finished product obtained by this method is low, and the reagents used are expensive. Among them, in the preparation of the key intermediate 2-chloro-3-trifluoroethoxymethyl-4-methanesulfobenzoic acid, potassium tert-butoxide is used as the base, the yield is low, and the reagent is expensive; The method needs to use the highly toxic reagent acetone cyanohydrin as the rearrangement catalyst, and needs to use thionyl chloride as t...

Claims

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Application Information

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IPC IPC(8): C07C315/04C07C317/24C07C317/46
CPCC07C315/04C07C317/46C07C317/24
Inventor 沈运河熊国银赵晓俊范富云
Owner HEFEI JIUYI AGRI DEV
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