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Preparation method of saflufenacil intermediate

A technology for saflufenacil and an intermediate, which is applied in the field of preparation of saflufenacil intermediates, can solve the problems of low yield, highly harmful and toxic reagent raw materials, complicated operation and the like, and achieves simple and good operation. Prospects for industrialization and the effect of less waste

Active Publication Date: 2021-03-30
NANJING LYNSCI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Therefore, aiming at the above content, the present invention provides a kind of preparation method of saflufenacil intermediate, solves the problem that the existing saflufenacil intermediate reaction process uses harmful toxic reagent raw materials, complicated operation and low yield. high problem

Method used

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  • Preparation method of saflufenacil intermediate
  • Preparation method of saflufenacil intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A preparation method of a saflufenacil intermediate, comprising the steps of:

[0035] a) Preparation of intermediate (1)

[0036] Dissolve 100g of methyl 2-chloro-4-fluoro-5-aminobenzoate and 108g of ethyl trifluoroacetoacetate in 500ml of toluene, then add 9.8g of sodium hydroxide, heat up to 100°C, react for 2h and then cool to room temperature , adding 1 mol / L dilute hydrochloric acid for washing, liquid separation, drying and concentration to obtain 150.1 g of intermediate (1), with a yield of 90%;

[0037] b) Preparation of intermediate (2)

[0038] Dissolve 150.1g of intermediate (1) and 45g of methylamine hydrochloride in 500ml of o-xylene, heat up to 140°C, react for 4 hours, cool to 0°C, and filter after crystallization to obtain 143.6g of intermediate (2) , yield 92%;

[0039] c) 2-chloro-4-fluoro-5-(3-methyl-2,6-dione-4-trifluoromethyl-2,3-dihydropyrimidinyl-1(6H)-yl)benzoic acid Preparation of methyl esters

[0040] Dissolve 143.6g of intermediate (2) ...

Embodiment 2

[0042] A preparation method of a saflufenacil intermediate, comprising the steps of:

[0043] a) Preparation of intermediate (1)

[0044] Dissolve 100g of methyl 2-chloro-4-fluoro-5-aminobenzoate and 134g of ethyl trifluoroacetoacetate in 500ml of chlorobenzene, then add 27g of sodium ethylate, heat up to 120°C for 3 hours, cool to room temperature, add Washing with 1 mol / L dilute hydrochloric acid, separating, drying and concentrating gave 151.9 g of intermediate (1), with a yield of 91%;

[0045] b) Preparation of intermediate (2)

[0046] Dissolve 151.9g of intermediate (1) and 55g of methylamine hydrochloride in 500ml of o-dichlorobenzene, heat up to 160°C for 5 hours, cool to 2°C, and filter after crystallization to obtain 143.9g of intermediate (2 ), yield 90%;

[0047] c) 2-chloro-4-fluoro-5-(3-methyl-2,6-diketone-4-trifluoromethyl-2,3-dihydropyrimidinyl-1(6H)-yl)benzoic acid Preparation of methyl esters

[0048] Dissolve 143.9g of intermediate (2) in 400ml of N,N-di...

Embodiment 3

[0050] A preparation method of a saflufenacil intermediate, comprising the steps of:

[0051] a) Preparation of intermediate (1)

[0052] Dissolve 100g of methyl 2-chloro-4-fluoro-5-aminobenzoate and 178g of ethyl trifluoroacetoacetate in 500ml of toluene, then add 47.6g of triethylamine, heat up to 140°C, react for 4 hours and then cool to room temperature , adding 1mol / L dilute hydrochloric acid for washing, liquid separation, drying and concentration to obtain 153.7g of intermediate (1), with a yield of 92%;

[0053] b) Preparation of intermediate (2)

[0054] 153.7g of intermediate (1) and 60g of methylamine hydrochloride were dissolved in 500ml of o-dichlorobenzene, heated to 180°C for 6 hours, cooled to 5°C, crystallized and filtered to obtain 148.4g of intermediate ( 2), yield 93%;

[0055] c) 2-chloro-4-fluoro-5-(3-methyl-2,6-diketone-4-trifluoromethyl-2,3-dihydropyrimidinyl-1(6H)-yl)benzoic acid Preparation of methyl esters

[0056] Dissolve 148.4g of intermediat...

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Abstract

The invention relates to the technical field of pesticide organic synthesis, and provides a saflufenacil intermediate preparation method, which comprises: a), carrying out reaction on 2-chloro-4-fluoro-5-aminobenzoate and ethyl 4,4,4-trifluoroacetoacetate to obtain an intermediate (1); b), reacting the intermediate (1) with methylamine hydrochloride to obtain an intermediate (2); and c), reactingthe intermediate (2) with an acylation reagent to obtain the 2-chlorine-4-fluorine-5-(3-methyl-2, 6-diketone-4-trifluoromethyl-2, 3-dihydropyrimidinyl-1(6H)- group) benzoate. The method solves the problems that toxic reagent raw materials with great harm are used in the existing saflufenacil intermediate reaction process, the operation is complicated, and the yield is not high.

Description

technical field [0001] The invention relates to the technical field of pesticide organic synthesis, in particular to a preparation method of a saflufenacil intermediate. Background technique [0002] Saflufenacil, molecular formula: C 17 h 17 CIF 4 N 4 o 5 S, its chemical name is: N'-[2-chloro-4-fluoro-5-(3-methyl-2,6-dione-4-(trifluoromethyl)-3,6-dihydro- 1(2H)-Pyrimidinyl)benzoyl]-N-isopropyl-N-methylsulfamide. Saflufenacil belongs to the pyrimidine class and is a protoporphyrinogen oxidase (PPO) inhibitor, which can effectively control more than 70 kinds of broad-leaved weeds in corn, sorghum, soybean, small grains, cotton, fruit trees and nuts, including Some weeds resistant to triazines, glyphosate and acetolactate synthase inhibitors have the advantages of good effect, low volatility, and safety to crops, and can be applied to various crop fields and non-cultivated land. [0003] 2-Chloro-4-fluoro-5-(3-methyl-2,6-dione-4-trifluoromethyl-2,3-dihydropyrimidinyl-1(...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/54
CPCC07D239/54
Inventor 陈正伟征玉荣沈晗于传宗
Owner NANJING LYNSCI CHEM
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