Synthesis method for prochloraz intermediate

A synthesis method and intermediate technology are applied in the field of prochloraz intermediate N-[2-ethyl]-N-n-propylamine, which can solve the problems of long amination reaction cycle, shortened reaction time, low yield and the like, Achieve the effect of eliminating vacuum distillation operation, shortening reaction time and saving cost

Inactive Publication Date: 2013-04-17
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to propose a kind of using ethanol as solvent, adopting Pd / γ-Al 2 o 3 Catalyst synthesis method, the new method greatly shortens the reaction time from 2 days to 8 hours

Method used

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  • Synthesis method for prochloraz intermediate
  • Synthesis method for prochloraz intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Take 26g of 2-(2,4,6-trichlorophenoxy)chloroethane in a 250mL three-necked flask, add 25mL of n-propylamine, 100mL of ethanol and 0.85g of catalyst Pd / γ-Al 2 o 3 (loading capacity 1%), reflux at 80 ° C, TLC tracking reaction, 8h reaction is complete, after the reaction ends, filter, get filter cake and filtrate, filter cake is soaked 24 hours with dehydrated alcohol, obtains the catalyst Pd / γ of recovery -Al 2 o 3 0.80g, the filtrate was decolorized with activated carbon, cooled to room temperature and then filtered, and the filtrate was evaporated to remove the solvent under reduced pressure to obtain the product N-[2-(2,4,6-trichlorophenoxy)ethyl]-N-n-propylamine 27.6g, yield 96%, purity 99% (detected by liquid chromatography).

Embodiment 2

[0035] Take 26g of 2-(2,4,6-trichlorophenoxy)chloroethane in a 250mL three-necked flask, add 50mL of n-propylamine, 130mL of ethanol and 0.78g of catalyst Pd / γ-Al 2 o 3 (Loading capacity 1%), reflux at 80 ℃, TLC tracking reaction, 8h reaction is complete, after the reaction finishes, filter, get filter cake and filtrate, filter cake soaks 48 hours with dehydrated alcohol, obtains the catalyst Pd / γ- Al 2 o 3 0.75g, the filtrate was decolorized with activated carbon, cooled to room temperature and then filtered, and the filtrate was evaporated to remove the solvent under reduced pressure to obtain the product N-[2-(2,4,6-trichlorophenoxy)ethyl]-N-n-propylamine 27.5g, yield 96%, purity 99.5% (detected by liquid chromatography).

Embodiment 3

[0037] Take 26g of 2-(2,4,6-trichlorophenoxy)chloroethane in a 250mL three-necked flask, add 15mL of n-propylamine, 52mL of ethanol and 1.3g of catalyst Pd / γ-Al 2 o 3 (loading capacity 2%), reflux under 80 ℃, TLC tracking reaction, 10h reaction is complete, after reaction finishes, filter, obtain filter cake and filtrate, filter cake soaks 48 hours with dehydrated alcohol, obtains the catalyst Pd / γ- Al 2 o 3 1.25g, the filtrate was decolorized with activated carbon, cooled to room temperature and then filtered, and the filtrate was evaporated to remove the solvent under reduced pressure to obtain the product N-[2-(2,4,6-trichlorophenoxy)ethyl]-N-n-propylamine 26.1g, yield 92%, purity 99.2% (detected by liquid chromatography).

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Abstract

The invention discloses a synthesis method for prochloraz intermediate which is N-[2-(2,4,6- trichlorophenoxy) ethyl]-N-propylamine. The synthesis method is as follows: dissolving 2-(2,4,6-trichlorophenoxy) chloroethane shown in formula II and propylamine in ethanol serving as a solvent; heating under the action of catalyst Pd / gamma-Al2O3 to reflux for reaction, carrying out TLC trace detection until reaction is finished completely, processing the reaction liquid to obtain the N-[2-(2,4,6-trichlorophenoxy) ethyl]-N-propylamine. The amount of substance ratio of 2-(2,4,6-trichlorophenoxy) chloroethane shown in formula II to propylamine is 1:2-6; the loading amount of Pd in the catalyst Pd / gamma-Al2O3 is 1-2wt%. In the invention, ethanol is utilized as the solvent, and Pd / gamma-Al2O3 is utilized as the catalyst, thus greatly shortening reaction time from original 2 days to 8h, and improving the purity, in addition, the conversion rate of raw materials is up to 100%, and the product yieldis up to as high as 96%.

Description

(1) Technical field [0001] The invention relates to a new method of prochloraz intermediate N-[2-(2,4,6-trichlorophenoxy)ethyl]-N-n-propylamine. (2) Background technology [0002] Prochloraz, also known as Shi Baoke, Shi Baogong, etc., the chemical name is N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-methanol Amide is a new type of imidazole broad-spectrum multi-purpose fungicide. It was developed by German Schering Agrochemical Co., Ltd. (now AgroEvo GmbH, Germany) in 1977. It has high bactericidal activity and is widely used in the control of rice, citrus, fruit trees, mushrooms and other various cereals and oil plants. , Vegetables and other crops of various diseases. It can also be widely used in the treatment of seeds and seedlings and the prevention and control of diseases in the storage period of post-harvest fruits. [0003] There are many preparation methods of prochloraz, and the process route is complicated. In 1975, US Patent No. 3 868 458 describe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/20C07C213/02
Inventor 熊静朱海峰江吉旺陈久喜吴华悦
Owner WENZHOU UNIV
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