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A method for preparing pinoxaden by "one pot method"

A technology of pinoxaden and pot cooking, which is applied in the field of "one pot cooking" to prepare pinoxaden, can solve the problems of increasing product production cost and environmental protection pressure, increasing the complexity of production operations, and long online reaction time, etc., to achieve reduction The effect of online reaction time, reduction of three wastes, and increase of conversion rate

Active Publication Date: 2021-10-19
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that the existing methods all separate the coupling reaction and the acylation reaction, which will inevitably increase the complexity of production operations, bring greater pressure on three wastes treatment and longer online reaction time, Thereby increasing the production cost of the product and the pressure on environmental protection

Method used

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  • A method for preparing pinoxaden by "one pot method"
  • A method for preparing pinoxaden by "one pot method"
  • A method for preparing pinoxaden by "one pot method"

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 2-(2,6-diethyl-4-methylphenyl) malonamide (2.5g, 10mmol), 1-oxo-4,5-diazepane (1.0g, 10mmol) and Catalytic amount (0.5mmol) of nano-magnesium oxide was added to 100mL of toluene, stirred and heated to 120°C, reacted for 10h, then cooled the reaction solution to room temperature, added triethylamine (2.0g, 20mmol), stirred, and then dripped while stirring Add pivaloyl chloride (1.4g, 12mmol), after dropping, continue to stir in the greenhouse for 5h, filter with suction, wash the filtrate with 5% hydrochloric acid aqueous solution and 10% sodium hydroxide aqueous solution respectively, separate the organic phase, dry, and filter The desiccant was removed, concentrated, and recrystallized from n-hexane to obtain 2.8 g of pinoxaden, with a yield of 70%.

[0022] MS(ESI)m / z[M+H] + = 401.2.

[0023] 1 H NMR (CDCl 3 )δ: 1.03(s,9H), 1.12(t,6H), 2.29(s,3H), 2.35~2.63(m,4H), 3.81~3.90(m,4H), 3.93(m,2H), 4.26 (m,2H), 6.88(s,2H).

Embodiment 2

[0025] 2-(2,6-diethyl-4-methylphenyl) malonamide (2.5g, 10mmol), 1-oxo-4,5-diazepane (1.0g, 10mmol) and Add a catalytic amount (0.5mmol) of nano-titanium oxide to 100ml of toluene, stir and heat to 120°C, react for 10h, then cool the reaction solution to room temperature, add triethylamine (2.0g, 20mmol), stir, and then drop while stirring Add pivaloyl chloride (1.4g, 12mmol), after dropping, continue to stir in the greenhouse for 5h, filter with suction, wash the filtrate with 5% hydrochloric acid aqueous solution and 10% sodium hydroxide aqueous solution respectively, separate the organic phase, dry, and filter The desiccant was removed, concentrated, and recrystallized from n-hexane to obtain 2.9 g of pinoxaden, with a yield of 72%.

[0026] MS(ESI)m / z[M+H] + = 401.2.

[0027] 1 H NMR (CDCl 3 )δ: 1.03(s,9H), 1.12(t,6H), 2.29(s,3H), 2.35~2.63(m,4H), 3.81~3.90(m,4H), 3.93(m,2H), 4.26 (m,2H), 6.88(s,2H).

Embodiment 3

[0029] 2-(2,6-diethyl-4-methylphenyl) malonamide (2.5g, 10mmol), 1-oxo-4,5-diazepane (1.0g, 10mmol) and Catalytic amount (0.5mmol) of nano-zirconia was added to 100ml of dioxane, stirred and heated to 110°C, reacted for 10h, then cooled the reaction solution to room temperature, added triethylamine (2.0g, 20mmol), stirred, and then Add pivaloyl chloride (1.8 g, 15 mmol) dropwise while stirring, continue to stir in the greenhouse for 5 h, filter with suction, wash the filtrate with 5% aqueous hydrochloric acid solution and 10% aqueous sodium hydroxide solution, and separate the organic phase. The desiccant was removed by filtration, filtered, concentrated, and recrystallized from n-hexane to obtain 2.4 g of pinoxaden with a yield of 60%.

[0030] MS(ESI)m / z[M+H] + = 401.2.

[0031] 1 H NMR (CDCl 3 )δ: 1.03(s,9H), 1.12(t,6H), 2.29(s,3H), 2.35~2.63(m,4H), 3.81~3.90(m,4H), 3.93(m,2H), 4.26 (m,2H), 6.88(s,2H).

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Abstract

The invention discloses a method for preparing pinoxaden by "one-pot cooking method". The method uses 2-(2,6-diethyl-4-methylphenyl) malonamide, 1-oxygen-4,5 ‑Diazepane and pivaloyl chloride are used as raw materials, and under the action of a catalyst, pinoxaden is prepared in one step through the "one-pot method". The general reaction formula is as shown in formula (1). The method of the invention has short route, simple operation and high conversion rate, can effectively reduce the amount of three wastes and online reaction time, and is very suitable for industrial production.

Description

technical field [0001] The invention relates to chemical synthesis, in particular to a new method for preparing pinoxaden by "one-pot cooking method". Background technique [0002] Pinoxaden belongs to the new phenylpyrazoline herbicides and is an inhibitor of acetyl-CoA carboxylase (ACC). It causes fatty acid synthesis to be blocked, cell growth and division to stop, cell membrane lipid-containing structure to be destroyed, and weeds to die. Pinoxaden was developed by Syngenta and launched in 2006. It is mainly used for grains and used after emergence to control gramineous weeds. Its global sales in 2010 were 230 million US dollars, and by 2015 its sales had reached about 500 million US dollars, ranking among the top ten herbicides in the world. [0003] There have been many public reports on the synthesis of pinoxaden. Yang Zihui et al. have made a relatively comprehensive review on the synthesis route of pinoxaden (Zhejiang Chemical Industry, 2017, 48(7):3-5), Bu Long, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04
CPCC07D498/04
Inventor 雷林李新松房雷
Owner SOUTHEAST UNIV
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