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A kind of preparation method of imidazoram

A technology of imidacloprid and trifluoromethyl pyridine, applied in the field of preparation of imidacloprid, can solve the problems of expensive catalyst and complicated process steps, and achieve the effects of reducing energy consumption of products, simplifying processes, and reducing operation steps.

Active Publication Date: 2022-03-01
YANGZHOU TIANHE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The prior art also discloses imidacloprone and its preparation method. The authorized announcement number is CN104876859B, and the authorized announcement date is 20180313. The method prepares 2,6-difluorobenzamide and oxalyl chloride to prepare 2,6-difluorophenyliso Nitrile ester; 2-chloro-5-nitrophenol and 2,3-bis-5-trifluoromethylpyridine etherification product and 2,6-difluorobenzene isocyanate to synthesize imidacloprone, this The process steps are cumbersome and the catalyst is expensive

Method used

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  • A kind of preparation method of imidazoram
  • A kind of preparation method of imidazoram
  • A kind of preparation method of imidazoram

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0029] (1) Put 60ml of toluene and 15.7g of 0.1mol 2,6-difluorobenzamide into the reaction kettle, start to add 15.2g of 0.12mol oxalyl chloride dropwise at 25°C, after the dropwise addition, adjust the temperature to 40-50°C and keep it warm React for 1 hour, heat preservation is over, slowly raise the temperature to slight reflux, and heat preservation reaction at 100-115°C for 5-6 hours; cool down to 10-30°C to prepare the standby liquid formula Ⅰ;

[0030] (2) 13.7 g of 0.095 mol of 2-chloro-5-aminophenol, 10.6 g of potassium carbonate of 0.077 mol, and 60 ml of toluene were stirred at room temperature for 30 min in a dry and clean reactor to obtain formula II;

[0031] (3) Add the reserve liquid formula I dropwise to the formula II, control the temperature at 15-35°C, add 0.1g of tetrabutylammonium bromide and 1.5ml of DMF after the drop, and stir at the temperature of 15-35°C for 24 hours to obtain the formula III;

[0032] (4) Add 20.4 g of 0.095 mol of 2,3-dichloro-5-...

Embodiment 2

[0034] (1) Put 60ml of toluene and 15.7g of 0.1mol 2,6-difluorobenzamide into the reaction kettle, start to add 23.6g of 0.15mol oxalyl chloride dropwise at around 25°C, after the dropwise addition, adjust the temperature to 40-50°C Heat preservation reaction for 1 hour, heat preservation is over, slowly raise the temperature to slight reflux, and heat preservation reaction at 100-115°C for 5-6 hours; distill toluene and excess oxalyl chloride under reduced pressure, cool down to 10-30°C, and prepare the standby liquid formula I;

[0035] (2) 14.0 g of 0.097 mol of 2-chloro-5-aminophenol, 12.1 g of 0.088 mol of potassium carbonate, and 60 ml of toluene were dropped into a dry and clean reactor, and stirred at room temperature for 30 min to obtain formula II;

[0036] (3) Add the reserve liquid formula I dropwise to the formula II, and control the temperature at 15-35°C; add 0.1g of tetrabutylammonium bromide and 1.5ml of DMF after dropping, and stir at the temperature of 15-35°...

Embodiment 3

[0039] (1) Put 60ml of toluene and 15.7g of 0.1mol of 2,6-difluorobenzamide into the reaction kettle, start to drop 28.3g of 0.18mol of oxalyl chloride at around 25°C, after the dropwise addition, adjust the temperature to 40-50 ℃ heat preservation reaction for 1 hour, after the heat preservation is over, slowly raise the temperature to slight reflux, and heat preservation reaction at 100-115 ℃ for 5-6 hours; cool down to 10-30 ℃ to prepare the standby liquid formula Ⅰ;

[0040] (2) 14.3 g of 0.099 mol of 2-chloro-5-aminophenol, 13.8 g of 0.10 mol of potassium carbonate, and 60 ml of toluene were dropped into a dry and clean reactor, and stirred at room temperature for 30 min to obtain formula II;

[0041] (3) Add the reserve liquid formula I dropwise to the formula II, and control the temperature at 15-35°C; add 0.1g of tetrabutylammonium bromide and 1.5ml of DMF after dropping, and stir at the temperature of 15-35°C for 24 hours to obtain the formula III;

[0042] (4) Add 2...

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Abstract

The invention discloses a preparation method of imidazoturon in the technical field of organic synthesis. The method comprises the following steps: (1) 2,6-difluorobenzamide reacts with oxalyl chloride to generate formula I, (2) in solvent toluene, 2-chloro-5-aminophenol reacts with potassium carbonate to generate formula II, (3) formula I and formula II react under the condition of catalyst to generate formula III, (4) formula III and 2,3-dichloro-5-trifluoromethylpyridine react to generate imidazoturon, the advantage of the present invention is to simplify the process steps to increase the yield.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of imidazoturon. Background technique [0002] Imidazuron, alias 1-(4-chloro-3-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-3-(2,6-difluorobenzoyl)urea , molecular formula: C 20 h 10 Cl 2 f 5 N 3 o 3 . Imidazuron is a new generation of high-efficiency benzoylurea insect growth regulator. As a veterinary drug, it is mainly used to kill ectoparasites in animals. It is a broad-spectrum antiparasitic drug with strong insecticidal and ovicidal activities. [0003] The prior art discloses a preparation method of the biological anthelmintic drug imidaclofen, the application publication number CN101209992, and the application publication date 20080702. The method uses 2-chloro-5-aminophenol, 2,6-dichlorobenzamide and oxalyl chloride as The raw material is a method for synthesizing imidacloprid through three-step pressurized reaction, which requi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/643
CPCC07D213/643
Inventor 张来平赵云德刘磊朱林飞黄正帅周杰
Owner YANGZHOU TIANHE PHARM CO LTD
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