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Pretilachlor synthesis method

A synthesis method and a technology of pretilachlor, applied in the field of chemistry, can solve the problems such as the inability to reuse the catalyst repeatedly, expensive platinum catalyst, etc., and achieve the effects of mild conditions, environmental friendliness and simple operation.

Inactive Publication Date: 2016-05-25
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] This method avoids the use of sulfuryl chloride reaction reagents, but requires the use of expensive platinum catalysts, and there are problems such as the catalysts cannot be reused and the recovery is difficult, especially the hydrogen reaction at a high temperature of 200 ° C, which has potential safety hazards

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0067] (1) In a 500ml three-necked flask, add 160mL of n-propanol and 30g (0.365mol) of sodium n-propoxide, stir, and after the sodium n-propoxide is completely dissolved, add 65mL (0.571mol) dropwise (30 minutes) 2-Chloroacetaldehyde dimethyl acetal, the temperature was raised to reflux after dropping, and the reaction was stirred for 6h. After cooling and filtering, the filtrate is distilled at normal pressure to recover n-propanol, and then distilled under reduced pressure by water pump to collect fractions at 70-80°C (-0.098MPa) to obtain the product - propoxyacetaldehyde dimethyl acetal (colorless liquid) 60.6 g, yield 81.9%, detected by GC, the content is 95%.

[0068] (2) In a 1000ml three-necked flask, add 10g of propoxyacetaldehyde dimethyl acetal (0.0641mol) and THF 40mL, cool down in an ice-salt bath to below 0°C, and dropwise add about 25mL of 5M hydrochloric acid solution (10 minutes to complete) (thereby adjusting the pH to be less than 1), after the dropwise ad...

Embodiment 2

[0072] (1) In a 500ml three-neck flask, add 160mL of toluene and 30g (0.365mol) of sodium n-propoxide, stir, add dropwise (30 minutes after the addition) 65mL (0.571mol) of 2-chloroacetaldehyde dimethyl acetal, dropwise The temperature was raised to reflux, and the reaction was stirred for 6h. After cooling and filtering, the filtrate was distilled at normal pressure to recover toluene first, then distilled under reduced pressure by a water pump, and the fraction at 70-80°C (-0.098MPa) was collected to obtain 56.8g of a colorless liquid product with a yield of 76.7%. The content was 94.3% by GC detection. .

[0073] (2) In a 1000ml three-neck flask, add 15g (0.0954mol) of propoxyacetaldehyde dimethyl acetal and THF60mL, cool down in an ice-salt bath to below 0°C, and dropwise add about 40mL of 5M sulfuric acid solution (dropping is completed in 20 minutes) (thereby adjusting the pH to be less than 1), after the dropwise addition was completed, the reaction was stirred at room...

Embodiment 3

[0077] (1) In a 500ml three-necked flask, add 250mL (2.2mol) of 2-chloroacetaldehyde dimethyl acetal, slowly add (30 minutes) 30g (0.365mol) sodium n-propoxide, stir, and heat up to 50~ 60 ° C, stirring the reaction for 6h. After cooling and filtering, the filtrate was distilled at normal pressure to recover unreacted 2-chloroacetaldehyde dimethyl acetal, and then distilled under reduced pressure by a water pump to collect fractions at 70-80°C (-0.098MPa) to obtain 45g of the product colorless liquid with a yield of 60.8 %, detected by GC, the content is 96.0%.

[0078] (2) In a 1000ml three-neck flask, add 15g (0.0972mol) propoxyacetaldehyde dimethyl acetal and THF 60mL, cool down in an ice-salt bath to below 0°C, add about 40mL of 5M acetic acid solution dropwise (20 minutes to complete) (thereby adjusting the pH to 2-3), after the dropwise addition was completed, the reaction was stirred at room temperature for 2 hours. Then it was extracted with dichloromethane, the lowe...

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Abstract

The invention discloses a pretilachlor synthesis method. The pretilachlor synthesis method comprises steps as follows: sodium propanolate is dissolved in an organic solvent I, 2-chloroacetaldehyde dimethyl acetal is added dropwise, and heat is preserved until the reaction is performed completely; propoxy acetaldehyde dimethyl acetal and tetrahydrofuran are mixed, aqueous acid is added, and heat is preserved until the reaction is performed completely; 3-propoxy propionaldehyde, 2,6-diethyl aniline and an organic solvent II are mixed, a catalyst is added, hydrogen is introduced until certain pressure is obtained, and heat is preserved until the reaction is performed completely; amidogen ether, a sodium hydroxide solution and methylbenzene are mixed, chloroacetyl chloride is added dropwise at certain temperature, heat is preserved until the reaction is performed completely, and pretilachlor is prepared. With the adoption of the method, high-quality pretilachlor can be obtained.

Description

technical field [0001] The invention belongs to the field of chemistry, in particular to a method for synthesizing pretilachlor. Background technique [0002] Pretilachlor (English name: Pretilachlor) is a high-efficiency, low-toxicity, selective bud herbicide, which belongs to the transporting herbicide. Its current global sales exceed 200 million US dollars, of which 80% of the market supply comes from Chinese companies. Its structure is shown in Formula 1: [0003] [0004] The current domestic production process of pretilachlor commonly used is: first convert the hydroxyl group in the ethylene glycol monopropyl ether (1) into an easy leaving group (LeavingGroup=LG) to generate the intermediate (2). Then, intermediate (2) is reacted with 2,6-diethylaniline to obtain monoalkylated intermediate (3). Finally, intermediate (3) undergoes acylation reaction with chloroacetyl chloride to obtain pretilachlor (4). [0005] [0006] Reagent=SOCl 2 ,MeSO 2 Cl,4-CH 3 C 6...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C233/18
CPCC07C41/48C07C45/513C07C213/02C07C231/02C07C233/18C07C43/303C07C47/198C07C217/08
Inventor 吴清来黄志真白鹏王甜甜赵建龙
Owner ZHEJIANG UNIV
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