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Preparation method of 4-(trifluoromethylthio)nitrobenzene

A technology of trifluoromethylthio and trifluoromethylmercaptan, which is applied in the fields of sulfide preparation and organic chemistry, and can solve problems such as high safety production equipment and operation requirements, unsatisfactory overall product yield, and complicated post-processing. , to achieve the effect of extending the continuous production cycle, improving safety and stability, and reducing reaction steps

Active Publication Date: 2015-05-13
JIANGSU LINGYUN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Regarding the total synthesis of 4-trifluoromethylthionitrobenzene, the existing process mainly adopts p-nitrochlorobenzene as a raw material, first prepares the corresponding anisole, then chlorates, and finally fluorides the preparation process. Chlorine, anhydrous hydrogen fluoride or antimony trifluoride and other fluorinating reagents are used in the process, which are highly toxic and require high equipment and operation for safe production. In addition, the post-treatment is more complicated and the steps are longer. The overall yield of the product is not satisfactory

Method used

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  • Preparation method of 4-(trifluoromethylthio)nitrobenzene

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Embodiment 1

[0022] Embodiment 1: Preparation of 4-trifluoromethylthionitrobenzene (I)

[0023] In the reactor, add p-nitroanisole (II) (153g, 1.0mol), DMF (1800g), stir well and then add sodium trifluoromethanethiolate (148.8g, 1.2mol) in batches. Heat up to 120°C, stir and react for 8 hours. After the reaction is complete, remove the insoluble matter by filtration, then distill off most of the solvent, pour the residue into water, add ethyl acetate (1224g) for extraction, separate the layers, and use anhydrous Sodium sulfate was dried, after filtering to remove the desiccant, the solvent was distilled off, the residue was distilled under reduced pressure, and the fraction at 114-125°C / 2660Pa was collected to obtain 4-trifluoromethylthionitrobenzene (I), 181.6g, The yield is about 81.4%.

[0024] 1H NMR (CDCl 3 , 400MHz) δ: 7.48-7.56 (2H, m), 8.05-8.18 (2H, m). m / z: 224 (M+H)+ Example 2: Preparation of 4-trifluoromethylthionitrobenzene (I)

Embodiment 2

[0024] 1H NMR (CDCl 3 , 400MHz) δ: 7.48-7.56 (2H, m), 8.05-8.18 (2H, m). m / z: 224 (M+H)+ Example 2: Preparation of 4-trifluoromethylthionitrobenzene (I)

[0025] Add p-nitroanisole (II) (153g, 1.0mol) and DMF (1250g) in the reactor, stir well and then add sodium trifluoromethanethiolate (124g, 1.0mol) in batches, and heat up after the addition to 60°C, stirred and reacted for 4 hours, after the reaction was completed, filtered to remove insoluble matter, then distilled off most of the solvent, poured the residue into water, added ethyl acetate (1224g) for extraction, separated liquids, and used anhydrous sulfuric acid for the organic phase Sodium drying, after filtering to remove the desiccant, the solvent was distilled off, the residue was distilled under reduced pressure, and the fraction at 114-125°C / 2660Pa was collected to obtain 4-trifluoromethylthionitrobenzene (I), 153.7g, The rate is about 68.9%.

[0026] 1H NMR (CDCl 3 , 400MHz) δ: 7.48-7.56 (2H, m), 8.05-8.18 (2H...

Embodiment 3

[0027] In the reactor, add p-nitroanisole (II) (153g, 1.0mol), DMF (1500g), stir well and then add sodium trifluoromethanethiolate (136.4g, 1.1mol) in batches. Heat up to 90°C, stir and react for 6 hours. After the reaction is complete, remove the insoluble matter by filtration, then distill off most of the solvent, pour the residue into water, add ethyl acetate (1224g) for extraction, separate the layers, and use anhydrous Sodium sulfate was dried, after filtering to remove the desiccant, the solvent was distilled off, the residue was distilled under reduced pressure, and the fraction at 114-125°C / 2660Pa was collected to obtain 4-trifluoromethylthionitrobenzene (I), 172.3g, The yield is about 77.2%.

[0028] 1H NMR (CDCl 3 , 400MHz) δ: 7.48-7.56 (2H, m), 8.05-8.18 (2H, m). m / z: 224(M+H)+Example 4

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Abstract

The invention provides a preparation method of 4-(trifluoromethylthio)nitrobenzene, which is implemented by reacting paranitroanisole with trifluoro-methanthiol at a temperature of 60-150 DEG C, so that 4-(trifluoromethylthio)nitrobenzene is obtained. According to the invention, products are prepared by adopting a new synthetic method, especially by taking new raw materials through a one-step process, the whole production process is normally operated, reaction conditions are mild, and the utilization of anhydrous hydrogen fluoride with large toxicity and corrosivity is effectively avoided, therefore, the method has a broad application prospect.

Description

technical field [0001] The invention relates to a preparation method of a veterinary drug toltrazuril intermediate, in particular to a method for preparing 4-trifluoromethylthionitrobenzene. Background technique [0002] In modern agriculture and animal husbandry, pesticides and veterinary drugs are widely used. Appropriate and appropriate use of pesticides has an important impact on the output and quality of related industries. The development of green pesticides is required in terms of environmental protection and drug efficacy, and this patent introduces a widely used pesticide veterinary drug intermediate 4-trifluoromethylthionitrobenzene, which can not only be used as The intermediate of the anticoccidial drug toltrazuril, this veterinary drug has many advantages such as fast metabolism in animals after drug withdrawal, complete metabolism in one week, and less resistance to drugs, which makes it have a very broad prospect in the veterinary drug market. Moreover, it is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/09C07C319/14
Inventor 凌青云张义文蒋忠良
Owner JIANGSU LINGYUN PHARMA
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