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Synthesis technique for toltrazuril

A technology of toltrazuril and a new process, applied in the directions of drug combination, organic chemistry, anti-infective drugs, etc., can solve the problems of difficulty in expanding the production capacity of enterprises, high hydrogenation reaction pressure, harsh process conditions, etc., and achieves low cost and raw materials. Easy-to-obtain, simple-to-equip effects

Active Publication Date: 2008-09-17
HUBEI LONGXIANG PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The above synthesis route reported by DE4239000 uses potassium carbonate instead of sodium hydroxide, which improves the condensation reaction process conditions, but the hydrogenation reaction pressure is high, and the highly toxic gas phosgene is still used in the isocyanation. The process conditions are harsh, the production cost is high, and the production capacity of the enterprise Difficult to expand

Method used

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  • Synthesis technique for toltrazuril
  • Synthesis technique for toltrazuril
  • Synthesis technique for toltrazuril

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Preparation of 3-methyl-4-(4-trifluoromethylthiophenoxy)nitrobenzene

[0026] The reaction equation is as follows:

[0027]

[0028] Put 233g (1.2mol) of p-trifluoromethylthiophenol, 220g (1.59mol) of anhydrous potassium carbonate and 384g (4.91mol) of DMSO into a reaction vessel for mixing, heat to an internal temperature of 90°C and stir for 15min. Within 30 minutes Add dropwise a solution of 206g (1.2mol) of 2-chloro-5-nitrotoluene in 384g (4.91mol) of DMSO, and react at 135°C for 3h. After the reaction is complete, evaporate the solvent under reduced pressure, and add 640ml of ice water after evaporation. , filtered, after the filter cake was dried, recrystallized with petroleum ether to obtain light yellow crystals, i.e. 342.6g (86.7%) of 3-methyl-4-(4-trifluoromethylthiophenoxy)nitrobenzene, mp 61-62°C.

[0029] (2) Preparation of 3-methyl-4-(4-trifluoromethylthiophenoxy)aniline

[0030] The reaction equation is as follows:

[0031]

[0032] 296.4 g ...

Embodiment 2

[0042] (1) Preparation of 3-methyl-4-(4-trifluoromethylthiophenoxy)nitrobenzene

[0043] Put 233g (1.2mol) of p-trifluoromethylthiophenol, 166g (1.2mol) of anhydrous potassium carbonate and 2.4mol of DMSO into the reaction vessel for mixing, heat to the inner temperature of 90°C and stir for 15min, and dropwisely add within 60 minutes A solution of 0.96 mol of 2-chloro-5-nitrotoluene in N,N-dimethylformamide (2.4 mol) was reacted at 155°C for 6 hours. After the reaction was completed, the solvent was evaporated under reduced pressure, and ice water was added after evaporation 640ml, filtered, dried the filter cake and recrystallized with petroleum ether to obtain light yellow crystals, i.e. 300.6g (85.7%) of 3-methyl-4-(4-trifluoromethylthiophenoxy)nitrobenzene, mp 61-62°C.

[0044](2) Preparation of 3-methyl-4-(4-trifluoromethylthiophenoxy)aniline

[0045] Mix 296.4 g (0.9 mol) of 3-methyl-4-(4-trifluoromethylthiophenoxy) nitrobenzene obtained in the previous step, 15 g (10...

Embodiment 3

[0051] (1) Preparation of 3-methyl-4-(4-trifluoromethylthiophenoxy)nitrobenzene

[0052] Put 1 mol of p-trifluoromethylthiophenol, 1.4 mol of anhydrous potassium carbonate and 6 mol of DMSO into a reaction vessel and mix, heat to an internal temperature of 90°C and stir for 15 minutes, and dropwise add 2-chloro-5-nitro within 90 minutes A solution of sulfolane (6 mol) with 1.2 mol of toluene was reacted at 135°C for 3 hours. After the reaction was completed, the solvent was evaporated under reduced pressure. After evaporation, 640 ml of ice water was added, filtered, and the filter cake was dried and recrystallized with petroleum ether to obtain shallow Yellow crystals, namely 3-methyl-4-(4-trifluoromethylthiophenoxy)nitrobenzene 340.6 g (87.7%), mp 61-62°C.

[0053] (2) Preparation of 3-methyl-4-(4-trifluoromethylthiophenoxy)aniline

[0054] The 3-methyl-4-(4-trifluoromethylthiophenoxy group) nitrobenzene 1.0mol, Pd / C15g (10%) obtained in the previous step are mixed with but...

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PUM

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Abstract

The invention relates to the field of chemically synthesized drug, in particular to a new synthetic process of drug for preventing and curing poultry coccidiosis, i.e., toltrazuirl. The synthetic process includes allowing trifluoromethylthiophenol and 2-chloro-5-nitrotoluene as raw material to condense, performing the reduction reaction with hydrogen in presence of Pd / C catalyst, reacting with bis (trichloromethyl) carbonate for esterifying isocyanic acid, and finally adding diethyl carbonate and methylurea for synthesizing toltrazuirl. The new synthetic process of toltrazuirl has easy operation, simple required equipment, low pollution, easily the prior raw material, low cost, and high yield with a total one of up to about 50%.

Description

technical field [0001] The invention relates to the field of chemical synthesis drugs, in particular to a new synthesis process of toltrazuril, a drug used for the prevention and treatment of poultry coccidiosis. technical background [0002] Toltrazuril is a triazinone anticoccidial drug developed by Bayer Company in Germany in the late 1980s. This product is mainly used for the prevention and treatment of fulminant coccidiosis. Poisonous, Eimeria tenella, Eimeria turkey glandularis, Eimeria turkey, Eimeria turkey minor all have killing effect. [0003] Literature reports, the synthetic preparation technology of toltrazuril mainly contains following three kinds of methods: [0004] [0005] This is a synthetic route reported by US4874860. The raw materials used, such as methyl isocyanate and chlorocarbonyl isocyanate, are not easy to obtain directly from the market. If they are self-made, phosgene (carbonyl chloride) will be used. The safety hazard of industrial product...

Claims

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Application Information

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IPC IPC(8): C07D251/30A61P33/02
Inventor 彭要武潘志权祝宏赵勇
Owner HUBEI LONGXIANG PHARMA TECH CO LTD
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