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Synthetic method of prothioconazole midbody 1-chloro-1-acetyl cyclopropane

A technology of prothioconazole and a synthetic method is applied in the new industrial synthesis field of 1-chloro-1-acetylcyclopropane, can solve the problems of high cost, high price of sodium ethoxide and butyrolactone, and achieves low cost, The effect of high reaction yield and cheap and easy-to-obtain raw materials

Active Publication Date: 2017-01-04
YANGZHOU TIANCHEN FINE CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In this route, the price of sodium ethoxide and butyrolactone is relatively high, and they are used in the first step reaction, resulting in high overall cost

Method used

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  • Synthetic method of prothioconazole midbody 1-chloro-1-acetyl cyclopropane
  • Synthetic method of prothioconazole midbody 1-chloro-1-acetyl cyclopropane
  • Synthetic method of prothioconazole midbody 1-chloro-1-acetyl cyclopropane

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Embodiment Construction

[0038] 1. Production process:

[0039] 1. Synthesis of intermediate compound (2):

[0040] Add compound (1) (223.5g, 1.72 mol) and acetone (1100 ml) into a three-neck round bottom flask, add solid sodium iodide (12.9g, 0.086 mol), 1,2-dichloroethane (681g, 8.88 mol) and anhydrous potassium carbonate (285g, 2.06mol), the temperature was raised to 55°C under the protection of nitrogen, and the stirring was maintained for 24 hours in a slightly boiling reflux state. The gas phase detection reaction showed that the conversion rate of compound (1) was greater than 96%, and the solvent acetone was concentrated and recovered. and dichloroethane, the residue was extracted with tert-butyl methyl ether, filtered, the solid was washed, the filtrate was washed with brine, dried and concentrated, and distilled under high vacuum to obtain 265g of compound (2), the gas phase purity was greater than 97%, and the yield was 80% %.

[0041] 2. Synthesis of intermediate compound (3):

[0042] ...

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Abstract

The invention relates to a synthetic method of a prothioconazole midbody 1-chloro-1-acetyl cyclopropan, which relates to the technical field of chemical production. The synthetic method comprises the following steps: mixing alkyl acetoacetate and 1,2-dihaloalkane or ethylene glycol disulfonate, performing mono-alkylation reaction, after chloration reaction, mixing with a strong acid, performing hydrolysis, and obtaining 3,5-dichloropentane-2-ketone or 3-chloro-4- sulfonate pentane-2-ketone; and finally taking quaternary ammonium salt as a catalyst, mixing the 3,5-dichloropentane-2-ketone or 3-chloro-4-sulfonate pentane-2-keton and alkali liquor, performing ring closing reaction, and obtaining 1-chloro-1-acetyl cyclopropane. By adopting the synthetic method, the cost is reduced, three wastes (waste water, waste gas and waste residues) are reduced, safety and reliability are realized, and the reaction yield is high.

Description

technical field [0001] The invention relates to the technical field of chemical production, in particular to a new industrial synthesis method of 1-chloro-1-acetylcyclopropane. Background technique [0002] Prothioconazole (common name: prothioconazole) is a new broad-spectrum triazolethione fungicide. Prothioconazole is mainly used to prevent and control many diseases of cereal crops such as wheat, barley, rapeseed, peanut, rice and bean crops. It has a good control effect on almost all wheat diseases, such as powdery mildew, sheath blight, fusarium wilt, leaf spot, rust, sclerotinia, net spot, moire, etc. of wheat and barley. It can also prevent and control soil-borne diseases of rapeseed and peanuts, such as sclerotinia, and major foliar diseases, such as gray mold, black spot, brown spot, black shank, sclerotinia and rust, etc. Good systemic activity, excellent protective, therapeutic and eradicating activities, and long-lasting. Prothioconazole not only has good safe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/67C07C49/327
CPCC07C45/67C07C49/327C07C45/676C07C67/307C07C67/343C07C49/16C07C69/72
Inventor 陈国云罗冶斌谢吉民王晨刘润兴
Owner YANGZHOU TIANCHEN FINE CHEM
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