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Novel technology of preparing thifluzamide from thiazole acid

A technology of thifluxamide and thiazole carboxylic acid, which is applied in the chemical field, can solve the problems of long reaction time and complicated reaction conditions, and achieve the effect of short reaction time and simple steps

Inactive Publication Date: 2018-05-22
YINGDE GREATCHEM CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, although the productive rate is greatly improved compared with the former, the reaction time is longer and the reaction conditions are complicated.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] The present embodiment prepares Thiofuramide according to the following steps:

[0015] Step 1: Mix 0.237 mol, 52.63 g of 2-methyl-4-trifluoromethyl-5-thiazolecarboxylic acid (content 95%) with 0.237 mol, 81 g of 2,6-dibromo-4-trifluoromethane Put oxyaniline (content 98%) in a certain amount of acetonitrile, raise the temperature to 50°C, and stir for about 0.5 h;

[0016] Step 2: Slowly add 0.242 mol of the catalyst and 33.2 g of phosphorus trichloride dropwise to the above-mentioned reactant. After the addition is completed, the temperature is raised to reflux, and the temperature is kept at reflux for reaction. The reaction is controlled until the reaction is almost complete, and the reaction time is about 10 h;

[0017] Step 3: The above product was lowered to room temperature, slowly dropped into a certain amount of crushed ice, and then stirred for 0.5 h to obtain the target product Thiofuramide. Filtered and dried, weighed: 109.7 g, detected purity: 92.08%, yiel...

Embodiment 2

[0019] Step 1: Mix 0.237 mol, 52.63 g of 2-methyl-4-trifluoromethyl-5-thiazolecarboxylic acid (95% content) with 0.261 mol, 89.2 g of 2,6-dibromo-4-trifluoromethane Add oxyaniline (content 98%) to a certain amount of acetonitrile, heat up to 55°C, and stir for about 0.5 h;

[0020] Step 2: Slowly add 0.261 mol of the catalyst and 40 g of phosphorus oxychloride dropwise to the above-mentioned reactants. After the addition is completed, the temperature is raised to reflux, and the temperature is kept at reflux for reaction. The reaction is controlled until the reaction is almost complete, and the reaction time is about 8 h;

[0021] Step 3: The above product was lowered to room temperature, slowly dropped into a certain amount of crushed ice, and then stirred for 0.5 h to obtain the target product Thiofuramide. Filtration and drying, weighing: 112.2 g, detected purity: 94.3%, yield: 84.6%.

Embodiment 3

[0023] Step 1: Mix 0.237 mol, 52.63 g of 2-methyl-4-trifluoromethyl-5-thiazolecarboxylic acid (95% content) with 0.4266 mol, 145.79 g of 2,6-dibromo-4-trifluoromethane Put oxyaniline (content 98%) in a certain amount of acetonitrile, raise the temperature to 60°C, and stir for about 0.5 h;

[0024] Step 2: Add 0.242 mol of catalyst and 34.35 g of phosphorus pentoxide to the above-mentioned reactants in batches. After the addition is completed, the temperature is raised to reflux, and the temperature is kept at reflux for reaction. The reaction is controlled until the reaction is almost complete, and the reaction time is about 8 h;

[0025] Step 3: The above product was lowered to room temperature, slowly dropped into a certain amount of crushed ice, and then stirred for 0.5 h to obtain the target product Thiofuramide. Filtration and drying, weighing: 90.65 g detected purity: 93.5%, yield: 67.79%.

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Abstract

The invention provides a novel technology of preparing thifluzamide from thiazole acid. The invention relates to a preparation method of a bactericide namely thifluzamide, and belongs to the technicalfield of chemistry. The invention discloses a one-step synthesis method of thifluzamide, and the synthesis method is simple and high efficient. According to the synthesis method, 2-methyl-4-trifluoromethyl-1,3-thiazole formic acid and 2,6-dibromo-trifluoromethoxyl aniline are taken as the primary raw materials, and the bactericide namely thifluzamide is synthesized in one step without any intermediate treatment in the presence of a catalyst. The novel technology has the advantages that the step is simple, there are few post treatment steps, and the reaction period is shortened.

Description

technical field [0001] The invention relates to a preparation method of a synthetic fungicide thifluzamide, which belongs to the field of chemical technology. Background technique [0002] Thiofuramide belongs to Thiofuramide fungicides, its chemical name is: 2,6-dibromo-2-methyl-4-trifluoromethoxy-4-trifluoromethyl-1,3-thiazole-5 - Formamide. Thiofuramide is a kind of fungicide developed by Monsanto Company of the United States. It can effectively control the diseases caused by Rhizoctonia, rust fungus and white silkworm; the treatment of seeds can effectively control the diseases caused by smut, Tilletia and striae, especially for the diseases caused by basidiomycete fungi such as sheath blight , Blight and other special effects. At present, regarding the preparation method from its intermediate 2-methyl-4-trifluoromethyl-5-thiazolecarboxylic acid to the final product thifluzamide, the prior art EP0371950A2 (28,11,1989) discloses the use of thionyl chloride to 2-Methyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/56
CPCC07D277/56
Inventor 吴晓霞刘世勇刘付康华彭军贾凤聪王世银
Owner YINGDE GREATCHEM CHEM
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