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Preparation method of 1-phenyl-3-(1, 2, 3-thiadiazol-5-yl)urea

A thiadiazole and phenyl technology, applied in the field of fine chemical industry, can solve the problems of high water content in post-treatment solvents, difficult reuse, poor reaction selectivity, etc., and achieve high product yield, good product quality, and mild and controllable reaction. Effect

Pending Publication Date: 2020-10-13
河南源博新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction selectivity is poor, the yield is low, the product content is low, generally around 95%, the post-treatment solvent has high water content, it is difficult to reuse, and dehydration treatment is required

Method used

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Examples

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Comparison scheme
Effect test

preparation example Construction

[0021] In some more specific embodiments, the preparation method includes the following steps:

[0022] Use 5-amino-1.2.3-thiadiazole as raw material, add anhydrous organic solvent, add phenyl isocyanate dropwise while stirring, cool down and react, add catalyst after dropwise addition, and then add N.N-dimethylethyl ether Amide, heated to 35-37°C while stirring, kept warm and reacted until the raw materials disappeared, stopped the reaction, lowered the temperature to below 15°C, carried out suction filtration, water washing and drying in sequence to obtain a light yellow solid, that is, 1-phenyl- 3-(1,2,3-thiadiazol-5-yl)urea; its reaction equation is as follows:

[0023] .

Embodiment 1

[0025] This embodiment provides a preparation method of 1-phenyl-3-(1,2,3-thiadiazol-5-yl)urea, the method comprising the following steps:

[0026] Using 1mol of 5-amino-1.2.3-thiadiazole as raw material, add 610ml of acetonitrile solvent, add 1.01mol of phenyl isocyanate dropwise while stirring, cool down and react, add triethylamine after the dropwise addition, and stir while Heat to 35°C, keep warm and react until the raw materials disappear, stop the reaction, cool down to 13°C, carry out suction filtration, water washing and drying in sequence to obtain 206g of light yellow solid, melting point mp212-224°C, yield 93.63%, light yellow solid That is 1-phenyl-3-(1,2,3-thiadiazol-5-yl) urea, acetonitrile is reclaimed from the mother liquor, water is removed with phosphorus pentoxide, and the solvent recycling rate is 85.6%; its reaction equation is as follows :

[0027] .

Embodiment 2

[0029] This embodiment provides a preparation method of 1-phenyl-3-(1,2,3-thiadiazol-5-yl)urea, the method comprising the following steps:

[0030] Add 102 g of dry 5-amino-1.2.3-thiadiazole into the dry reactor, add 500 ml of anhydrous toluene, and add 120.5 g of phenyl isocyanate dropwise while stirring. After the dropwise addition is completed, add cold water to the jacket layer of the reactor to lower the temperature to 30°C, keep warm and react. After the dropwise addition, add 1g of catalyst-methylamine, then add 10g of N.N-dimethylacetamide, and stir for 15 minutes, turn off the cooling water, slowly heat to 36°C, keep warm and react for 4 hours, stop the reaction until the HPLC detects that the raw materials disappear, cool down to 10°C, perform suction filtration, water washing and drying in sequence to obtain 216g of light yellow solid, melting point mp212 -224°C, yield 98.1%, the light yellow solid is 1-phenyl-3-(1,2,3-thiadiazol-5-yl)urea, toluene is recovered from...

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Abstract

The invention relates to a preparation method of 1-phenyl-3-(1, 2, 3-thiadiazol-5-yl)urea. The preparation method comprises the following steps: by using 5-amino-1, 2, 3-thiadiazole as a raw material,adding a composite solvent, reacting the raw material with phenyl isocyanate, and sequentially carrying out suction filtration, washing and drying to obtain a faint yellow solid, thereby obtaining the 1-phenyl-3-(1, 2, 3-thiadiazol-5-yl)urea. The preparation method disclosed by the invention has the beneficial effects that the reaction conditions are mild and controllable, the yield is high, andthe quality of the obtained product is excellent; and the solvent is high in boiling point, not easy to dissolve in water, convenient to recover and less in loss, so the preparation method less in equipment investment and short in production period, the solvent recovery rate is 95% or above, and the product yield is high.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and relates to a synthesis method of a growth regulator intermediate, in particular to a preparation method of 1-phenyl-3-(1,2,3-thiadiazol-5-yl)urea . Background technique [0002] 1-Phenyl-3-(1,2,3-thiadiazol-5-yl)urea is an important growth regulator intermediate, which has a strong activity of promoting plant cell division, and is widely used in economic plants such as cotton and grapes . It has the characteristics of broad spectrum, high efficiency, low toxicity and low residue, and is friendly to the environment. It is often used as a defoliant before cotton harvest abroad. This product is developed by developed countries such as Europe and the United States. Its production process is long and complex, with harsh process conditions, high technical requirements, and difficult production. The preparation of 1-phenyl-3-(1,2,3-thiadiazol-5-yl)urea usually adopts 5 amino-1.2.3-thiadiaz...

Claims

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Application Information

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IPC IPC(8): C07D285/06
CPCC07D285/06
Inventor 徐在礼王满仓刘双思徐伟岳彩瑞张永旺常文利王枫张付杰
Owner 河南源博新材料有限公司
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