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Preparation method of 2-thioether-N, N-dimethyl nicotinamide

A dimethyl nicotinamide and sulfide-based technology, which is applied in the field of pesticides, can solve the problems that it is difficult to scale up to the production stage, and achieve the effects of less three wastes, obvious cost advantages, and favorable industrialization

Pending Publication Date: 2021-08-06
江苏先导药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002]2-thioether-N,N-dimethylnicotinamide is often used in the synthesis of medicines and pesticides, especially as the intermediate of the herbicide nicosulfuron The body has received much attention and research. The synthesis method in the prior art mainly uses 2-chloro-N,N-dimethylnicotinamide, sodium hydrosulfide / sulfur or sodium sulfide / sulfur or thiourea as raw materials, high temperature substitution, It is prepared by acidification to obtain mercaptan intermediates, and then condensed with halides. During the process, a large amount of toxic gas hydrogen sulfide or ammonia is released, and it is difficult to increase the volume to the production stage.

Method used

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  • Preparation method of 2-thioether-N, N-dimethyl nicotinamide
  • Preparation method of 2-thioether-N, N-dimethyl nicotinamide
  • Preparation method of 2-thioether-N, N-dimethyl nicotinamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (Example 1) 2-benzylthio-N'N-dimethylnicotinamide

[0019]

[0020] Preparation of the target product in a small test:

[0021] Put 38.6g (0.20mol) of 2-chloro-N,N-dimethylnicotinamide, 99.2g (0.4mol) of sodium thiosulfate pentahydrate, 21.6g (0.20mol) of benzyl alcohol, and 2mL of water into a 500mL four-necked bottle , xylene 100g, heat and stir, reflux at 120-140°C for 5h, lower the temperature, add 50mL of water, separate the liquid to obtain an oil layer, recover the xylene and distill under reduced pressure to obtain >98% of the target 2-benzylthio-N' N-dimethylnicotinamide 480g, yield 88%.

Embodiment 2

[0022] (Example 2) 2-benzylthio-N'N-dimethylnicotinamide

[0023]

[0024] Preparation of target product in pilot scale:

[0025] Put 386kg of 2-chloro-N,N-dimethylnicotinamide, 1000kg of sodium thiosulfate pentahydrate, 216kg of benzyl alcohol, 20kg of water, and 1000kg of xylene into a 3000L enamel reaction kettle, slowly raise the temperature to reflux, and keep warm for 5 hours to complete the reaction , drop the temperature to 60 degrees, add 500kg of water dropwise, separate the liquid to obtain the oil layer, first normal pressure and then vacuum distillation to reclaim xylene, the recovery rate is 92%; after recovery, vacuum distillation obtains >98% of the target 2-benzylthio-N 'N-dimethylnicotinamide 460kg, yield 85%.

Embodiment 3

[0026] (Example 3) 2-thioether-N'N-dimethylnicotinamide

[0027]

[0028] Preparation of the target product in a small test:

[0029] Part of the results of parallel reaction optimization for different substituents to obtain alcohols are as follows:

[0030] serial number alcohol solvent yield 1 1-butanol Xylene 54％ 2 1-pentanol water 76％ 3 1-octanol DMSO 80％ 4 phenol DMF 57％

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Abstract

The invention relates to a preparation method of 2-thioether-N, N-dimethyl nicotinamide. The preparation method comprises the following steps: adding 2-chloro-N, N-dimethyl nicotinamide and sodium thiosulfate pentahydrate into an organic solvent at a certain temperature, and carrying out condensation substitution reaction on substituent-containing alcohol by a one-pot method to obtain the product 2-thioether-N, N-dimethyl nicotinamide. The method provided by the invention has the advantages of many raw material sources, obvious cost advantage, safer and more convenient preparation method, high total yield and less three wastes, especially no emission of toxic gases such as ammonia gas or hydrogen sulfide, and is beneficial to industrialization.

Description

technical field [0001] The present invention relates to the field of pesticides, relates to the synthesis technology of nicosulfuron intermediate, in particular to a preparation method of 2-thioether-N,N-dimethylnicotinamide. Background technique [0002] 2-thioether-N,N-dimethylnicotinamide is often used in the synthesis of medicines and pesticides, especially as an intermediate of the herbicide nicosulfuron, which has received much attention and research. The synthesis method in the prior art It is mainly prepared by using 2-chloro-N,N-dimethylnicotinamide, sodium hydrosulfide / sulfur or sodium sulfide / sulfur or thiourea as raw materials, high-temperature substitution and acidification to obtain thiol intermediates, and then condensed with halogenated compounds , A large amount of toxic gas hydrogen sulfide or ammonia is released during the process, and it is difficult to increase the amount to the production stage. Contents of the invention [0003] The purpose of the p...

Claims

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Application Information

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IPC IPC(8): C07D213/82
CPCC07D213/82
Inventor 陈月霞肖石基
Owner 江苏先导药业有限公司
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