Tebuthiuron synthesis method

A technology of tebuthiuron and synthetic method, which is applied in the field of organic synthesis, and can solve the problems of high toxicity of reaction raw materials, high safety risks, and difficulties in industrial operation

Active Publication Date: 2016-06-15
JIANGSU CHANGLONG AGROCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The present invention provides a method for synthesizing terbuthiauron with low toxicity of raw materials and easy industrial production, aiming at the problems of high toxicity of reaction raw materials, high safety risks and difficulties in industrial operation in the prior art.

Method used

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Embodiment 1

[0025] Add 200g of toluene, 100g (0.54mol) of 5-tert-butyl-2-chloro-1,3,4-thiadiazole, 52.6g (0.59mol, 1.1eq) of 1,3-dimethylurea into the reaction flask , stir evenly, heat up to 60°C, add dropwise 30% aqueous sodium hydroxide solution 86g (0.65mol, 1.2eq), continue to insulate for 5 hours after the dropwise addition, complete the reaction, separate layers, continue to wash the toluene phase twice, and remove the solvent. About 150g of toluene was extracted, cooled to 0°C and left to stand for 6 hours, the product precipitated, and 120g of white solid was obtained by suction filtration, which was verified as Tebuthiauron by mass spectrometry and hydrogen spectrometry, and its purity was 97% by HPLC, and the yield was 94.4 %.

Embodiment 2

[0027] Add 300g of chlorobenzene, 100g (0.54mol) of 5-tert-butyl-2-chloro-1,3,4-thiadiazole, 55g (0.62mol, 1.15eq) of 1,3-dimethylurea into the reaction flask , Potassium Carbonate 90g (0.65mol, 1.2eq), stir evenly, slowly heat up to 50°C, keep warm for 3 hours, after the reaction is complete, add water and stir to separate layers, continue to wash the chlorobenzene phase twice with water, and precipitate about 250g of chlorobenzene , cooled to 10°C and left to stand for 4 hours, the product precipitated, and 115g of white solid was obtained by suction filtration, which was verified as Tebuthiauron by mass spectrometry and hydrogen spectrometry, and its purity was 96% by HPLC, and the yield was 90.0%.

Embodiment 3

[0029] Add 500 g of dichloromethane, 100 g (0.54 mol) of 5-tert-butyl-2-chloro-1,3,4-thiadiazole, 57.4 g (0.64 mol, 1.2 eq), stir evenly, slowly raise the temperature to 40°C, add 77g (0.77mol, 1.4eq) of triethylamine dropwise, and keep warm for 8 hours. , about 450g of dichloromethane was released, cooled to 20°C and left to stand for 4 hours, the product was precipitated, and 113g of white solid was obtained by suction filtration, which was verified as Tebuthiauron by mass spectrometry and hydrogen spectrometry, and its purity was 96% as detected by HPLC. Yield 88.0%.

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Abstract

The invention provides a tebuthiuron synthesis method. Tebuthiuron is obtained by reaction between 1,3-dimethylurea and 5-tert-butyl-1,3,4-thiadiazole derivatives under the alkaline condition. The tebuthiuron synthesis method solves the problems of safety risks caused by use of extremely toxic substances such as methyl isocyanate and N-methyl formylchloride, presence of phosgene or the like, difficulty in production operation in traditional methods.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of terbuthiauron. Background technique [0002] The common name of tebuthiuron is tebuthiuron, also known as tebuthiuron, and its chemical name is 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea. Tebuthiauron technical appearance is white powder solid, melting point: 162°C, solubility in water is 2.5g / L (25°C), solubility in methanol is 170g / L (25°C). It is a total urea herbicide, which has good control effect on annual and perennial grasses and broad-leaved weeds. Mainly used to control weeds in non-arable land, shrubs in pastures, gramineous and broad-leaved weeds in sugarcane fields. [0003] Tebuthiauron mainly has three synthetic methods according to domestic and foreign literature reports. [0004] 1. US4283543, DE3113328, DE3314190, GB1195672 and other literature reports all use 5-tert-butyl-2-methylamino-1,3,4-thiadiazole to react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/135
CPCC07D285/135
Inventor 罗进超李有温泰伟汪强敏
Owner JIANGSU CHANGLONG AGROCHEM CO LTD
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