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Synthesis method of saflufenacil key intermediate

A technology of saflufenacil and a synthesis method, applied in the field of carbamate synthesis, can solve problems to be developed and the like, achieve the effects of high product yield, control of chlorinated isomers, and improved product purity

Pending Publication Date: 2022-05-13
安徽宁亿泰科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] For those skilled in the art, if non-chlorine raw materials are to be used to reduce the industrial production cost of saflufenacil, there must be suitable chlorination route and scheme support, so high yield and high selectivity synthesize polysubstituted aromatic amine derivatives The carbamate method remains to be developed

Method used

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  • Synthesis method of saflufenacil key intermediate
  • Synthesis method of saflufenacil key intermediate
  • Synthesis method of saflufenacil key intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the synthesis of selective chlorination reaction raw material

[0041](1) Synthesis of N-(3-nitro-4-fluorobenzoyl)-N’-methyl-N’-isopropylsulfonamide

[0042]

[0043] In 60ml of toluene, add N-methyl-N-isopropylaminosulfonamide (16.74g, 0.11mol), catalyst dimethylaminopyridine (72.0mg, 0.6mmol), acid-binding agent triethylamine (24.5g, 0.24mol), stirred and dissolved, then heated to 70°C, under nitrogen atmosphere, added the toluene solution of 3-nitro-4-fluorobenzoyl chloride (20.4g, 0.10mol) dropwise to the reaction system, added dropwise for 1h, after the dropwise addition was completed The suspension was cooled to room temperature and stirring was continued for 2 hours. The mixture was acidified by adding concentrated hydrochloric acid and stirred for 1 hour, the precipitated salt was filtered, washed once with 1N HCl solution, and the resulting wet solid was recrystallized by adding 50 g of chlorobenzene. Finally filter and dry under reduced pres...

Embodiment 2

[0047] Example 2: Synthesis of N-(5-amino-2-chloro-4-fluorobenzoyl)-N'-methyl-N'-isopropylsulfonamide

[0048]

[0049] Add N-(4-fluoro-3-aminobenzoyl)-N'-methyl-N'-isopropylsulfonamide (2.89g, 10mmol, 1.0eq), N-chlorobutanedi Imide (4.05g, 30mmol, 3.0eq) was dissolved in 100mL acetonitrile and stirred for 30min; dimethyl disulfide (1.22g, 13.0mmol, 1.3eq) was added at room temperature 25°C under nitrogen atmosphere. After the generated product was stirred and reacted at room temperature under a nitrogen atmosphere for 0.5-1h (monitored by LC), the reaction was basically converted, and concentrated by precipitation under negative pressure. The residual liquid was subjected to column chromatography (PE:EA=1:2) to obtain 2.90 g of the target compound at ~162°C, the product is a light yellow solid, the yield is 87%, and the HPLC purity is 97%.

Embodiment 3

[0050] Example 3: Synthesis of N-(5-amino-2-chloro-4-fluorobenzoyl)-N'-methyl-N'-isopropylsulfonamide

[0051] Add N-(4-fluoro-3-aminobenzoyl)-N'-methyl-N'-isopropylsulfonamide (2.89g, 10mmol, 1.0eq), N-chlorobutanedi Imide (4.05g, 30mmol, 3.0eq) was dissolved in 100mL dichloromethane and stirred for 30min; dimethyl disulfide (1.22g, 13.0mmol, 1.3eq) was added at room temperature 25°C under nitrogen atmosphere. After the generated product was stirred and reacted at room temperature under a nitrogen atmosphere for 0.5-1h (monitored by LC), the reaction was basically converted, and concentrated by precipitation under negative pressure. The residual liquid was subjected to column chromatography (PE:EA=1:2) to obtain 2.87g of the target compound at ~162°C, the product is a light yellow solid, the yield is 85%, and the HPLC purity is 96%. 1 H-NMR (400MHz, DMSO-d 6 )δ11.91(br s,1H),7.26(d,J=8.0Hz,1H),6.85(d,J=8.0Hz,1H),5.60(s,2H),4.10-4.06(m,1H) , 2.81 (s, 3H), 1.12 (d, J=8.0Hz, ...

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Abstract

The invention belongs to the field of synthesis of pesticide intermediates, and particularly relates to a synthesis method of saflufenacil key intermediate polysubstituted arylamine-derived carbamate. The preparation method comprises the following specific steps: taking N-(3-amino-4-fluorobenzoyl)-N '-methyl-N'-isopropyl sulfonamide as a raw material, and preparing N-(5-amino-2-chloro-4-fluorobenzoyl)-N '-methyl-N'-isopropyl sulfonamide with high yield and high selectivity in the presence of an additive; and further reacting with chloroformate to obtain the saflufenacil key intermediate. According to the synthesis method, use of expensive raw materials is avoided, the whole route is economical and environmentally friendly, and the product yield is high; the method is simple in process and good in selectivity, effectively controls the generation of chlorinated isomers, improves the product purity, greatly reduces the cost, and is more beneficial to the industrial production of saflufenacil.

Description

technical field [0001] The invention belongs to the field of synthesis of pesticide intermediates, and in particular relates to a method for synthesizing carbamates derived from polysubstituted aromatic amines, the key intermediate of saflufenacil. Background technique [0002] Saflufenacil is a protoporphyrinogen oxidase (PPO) inhibitor, which belongs to a new type of uracil stem and leaf treatment agent. A new level of foliar weed control". First of all, it can be applied to a variety of production systems and non-cultivated land, and can be used post-emergence or pre-emergence; second, it is applicable to many crops, including cereals, corn, cotton, rice, sorghum, soybeans, and fruit trees. more than 30 kinds of crops; thirdly, it has a wide control spectrum and can control more than 90 kinds of broad-leaved weeds, including some weeds resistant to triazines, glyphosate and acetolactate synthase inhibitors; Grass amine has many characteristics such as rapid control effe...

Claims

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Application Information

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IPC IPC(8): C07C303/34C07C307/06C07D239/54
CPCC07C303/34C07D239/54C07C307/06Y02P20/55
Inventor 张璞施立鑫其他发明人请求不公开姓名
Owner 安徽宁亿泰科技有限公司
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