Preparation method for isoxazoline-containing uracil compound

A technology for oxazoline uracil and compound is applied in the field of preparation of isoxazoline uracil-containing compounds, and can solve problems such as hindering the popularization and application of compounds, difficult industrial production of compounds, and inability of preparation methods to meet industrial production.

Pending Publication Date: 2018-09-25
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method for preparing such compounds is mentioned in the patent, the ring-closing reagents used in the preparation method, such as dichloromethylene dimethyl ammonium chloride, are not industrially produced on a large scale and are expensive, resulting in the It shows that the compound is not easy for industrial production; at the same time, in the preparation process, the ring is first closed and then methylated, and column chromatography is required, which is not easy for industrialization
[0005] In recent years, even though the isoxazoline-containing uracil compound shown in general formula I has good herbicidal activity, the existing preparation methods cannot meet the requirements of industrial production, thus hindering the popularization and application of the compound

Method used

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  • Preparation method for isoxazoline-containing uracil compound
  • Preparation method for isoxazoline-containing uracil compound
  • Preparation method for isoxazoline-containing uracil compound

Examples

Experimental program
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Effect test

Embodiment 1

[0065] The synthesis (1) of embodiment 1 compound I-1

[0066]

[0067] Sodium hydride (60%, 80g, 2mol) was added to 500mL DMF, and a mixed solution of trifluoroamino crotonate (compound IV-1, 98%, 186g, 1mol) and 120mL DMF was added dropwise under ice cooling for 1.5 hours After completion of the dropwise addition, warm up to room temperature (20-25°C) and stir for 1 hour, add dimethylcarbamoyl chloride (97%, 166g, 1.5mol) dropwise under ice-bath conditions, stir at room temperature for 3-4 hours, TLC monitors that the reaction is complete . Evaporate most of the DMF under reduced pressure, pour it into 500mL saturated aqueous sodium bicarbonate solution, and extract twice with 600mL ethyl acetate successively, combine the ethyl acetate phase, add 100g diatomaceous earth to the Buchner funnel to filter, and decompress After distillation, 238 g of oil was obtained, namely compound III-1, with a purity of 96.7% (HPLC normalized content), and a yield of 90.6%.

[0068] 238g...

Embodiment 2

[0069] The synthesis (2) of embodiment 2 compound I-1

[0070] Potassium tert-butoxide (98%, 172g, 1.5mol) was added to 650mL DMF, followed by trifluoroamino crotonate (compound IV-1, 98%, 186g, 1mol), stirred at room temperature (20-25°C) for 1 After 1 hour, dimethylcarbamoyl chloride (97%, 166 g, 1.5 mol) was added dropwise, stirred at room temperature for 5 hours, and the reaction was complete as monitored by TLC. Evaporate most of the DMF under reduced pressure, pour it into 500mL water, and extract twice with 600mL ethyl acetate, combine the ethyl acetate phase, add 100g of diatomaceous earth to the Buchner funnel, filter, and distill under reduced pressure to obtain 228g of oil That is compound III-1, the purity is 95% (HPLC normalized content), and the yield is 85.3%.

[0071]228g of compound III-1 (96.7%, 0.853mol) and 270g of compound II-1 (synthesized with reference to WO2016095768, 90%, 0.81mol) were successively added to a reaction flask containing 600ml of acetic...

Embodiment 3

[0072] The synthesis (1) of embodiment 3 compound 1-2

[0073]

[0074] Sodium hydride (60%, 80g, 2mol) was added in 500mL DMF, and a mixed solution of trifluoromethylamino crotonate (compound IV-2, 97%, 203g, 1mol) and 120mL DMF was added dropwise under ice-cooling, and after 1.5 Add dropwise after 1 hour, raise to room temperature (20-25°C) and stir for 1 hour, add dimethylcarbamoyl chloride (97%, 166g, 1.5mol) dropwise under ice-bath conditions, stir at room temperature for 3-4 hours, monitor the reaction by TLC completely. Evaporate most of the DMF under reduced pressure, pour it into 500mL saturated aqueous sodium bicarbonate solution, and extract twice with 600mL ethyl acetate successively, combine the ethyl acetate phase, add 100g diatomaceous earth to the Buchner funnel to filter, and decompress The distillation obtained 253g of oily substance which was compound III-2, with a purity of 97.2% (HPLC normalized content), and a yield of 91.8%.

[0075] 253g of compoun...

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PUM

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Abstract

The invention provides a preparation method for an isoxazoline-containing uracil compounds, belonging to the field of organic synthesis. The preparation method comprises the following steps: reactinga compound IV with an alkali in an organic solvent, then adding N,N-dimethylformyl chloride for a reaction so as to obtain a compound III and then reacting the compound III with a compound II in acidto obtain the target compound I. A reaction formula is as described in the specification. Each group in the formula is as described in the specification. The preparation method provided by the invention can avoid the use of expensive reagents or high-toxicity methylation reagents, effectively reduces cost and is easy for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of uracil compounds containing isoxazoline. Background technique [0002] Patent WO2016095768 reports isoxazoline-containing uracil compounds as shown in general formula I: [0003] [0004] The compound of general formula I has good herbicidal activity, and can effectively control barnyardgrass, foxtail, heteromorphous sedge, water sedge, crabgrass, weed grass, velvetleaf, zinnia, retroflexus, purslane, Weeds such as ears, black nightshade, cassia, wild watermelon seedlings, and wild soybeans can achieve good herbicide effects at low doses, and can be used as herbicides in agriculture. Although the method for preparing this type of compound is mentioned in the patent, the ring-closing reagent used in the preparation method, such as methylene chloride dimethyl ammonium chloride, is not industrially produced on a large scale and is expensive, r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10
CPCC07D413/10
Inventor 杨吉春武恩明金守征吴峤英君伍杨帆刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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