Preparation method for 1-methyl-5-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-biuret, and application thereof

A technology of trifluoromethylthio and phenoxy, applied in 1-methyl-5-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-condensate The preparation and application of diurea can solve the problems of poor safety and low yield, and achieve the effects of mild conditions, high conversion rate and simple process

Active Publication Date: 2012-10-17
ZHEJIANG GUOBANG PHARMA
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  • Abstract
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  • Claims
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Problems solved by technology

[0012] Although this patent uses solid phosgene to replace highly toxic phosgene, solid phosgene will still release phosgene when it encounters aniline com

Method used

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  • Preparation method for 1-methyl-5-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-biuret, and application thereof

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Embodiment 1

[0024] Example 1, the preparation of N-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-urea: 29.9g (0.1mol) arylamine was dropped into a four-necked flask , 30g water, 60g ethanol, 19.5g (0.3mol) sodium cyanate, control the temperature between 15-20 ℃ and drop 52.0g concentration of 35% hydrochloric acid (0.5mol), control the dropwise addition within 1 hour, and then Raise the temperature to 30°C for 2 hours, cool to 0°C and filter with suction, and dry the product under reduced pressure to obtain 33.0g of aryl urea with a conversion rate of 96.5%.

Embodiment 2

[0025] Example 2, N-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-urea preparation: 29.9g (0.1mol) arylamine was put into a four-necked flask, 30g Water, 60g (1mol) of glacial acetic acid, dissolve 9g (0.11mol) of potassium cyanate in 30g of water, add the aqueous solution of potassium cyanate dropwise at a temperature of 0°C, and control the dropwise addition within 3 hours. ℃ for 1 hour, and then heated to 50 ℃ for 0.5 hours, then cooled to room temperature and suction filtered, the filter cake was washed with a large amount of water and glacial acetic acid, and then dried under reduced pressure to obtain 31.5g of aryl urea, the conversion rate was 92.1%.

Embodiment 3

[0026] Example 3, N-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-urea preparation: put 29.9g (0.1mol) arylamine in a four-necked flask, 60g water, 299g chloroform, 17.3g phosphoric acid (0.15mol) with a concentration of 85%, add a saturated solution containing 32.5g (0.5mol) sodium cyanate dropwise at a controlled temperature between 45-50°C, and add dropwise within 1 hour After completion, the temperature was maintained at this temperature for 2 hours, cooled to 0° C. and suction filtered, and the product was dried under reduced pressure to obtain 30.5 g of aryl urea, with a conversion rate of 89.2%.

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Abstract

The present invention mainly discloses a preparation method for 1-methyl-5-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-biuret, and an application thereof. According to the present invention, 3-methyl-4-(4-trifluoromethylthio-phenoxy)-aniline reacts with a cyanate in the presence of an acid to obtain N-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-urea; the N-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-urea reacts with methylaminoformyl chloride in a solvent to obtain 1-methyl-5-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-biuret; the 1-methyl-5-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-biuret and diethyl carbonate are subjected to condensation under an alkaline condition to obtain an anti-coccidian drug toltrazuril. The method of the present invention has characteristics of simple process, mild conditions, high total conversion rate, good product quality, cheap and available raw materials, and green environmental protection, and is a competitive industrialization synthesis route.

Description

technical field [0001] The present invention relates to a key intermediate of toltrazuril, 1-methyl-5-[3-methyl-4-(4-trifluoromethylthio-phenoxy)-phenyl]-biuret Preparation. Background technique [0002] Toltrazuril is an anticoccidial drug developed by Bayer AG in Germany in the late 1980s, with a trade name of Baycox (Baiqiuqing). It interferes with the division of the parasite nucleus and mitochondrial respiratory metabolism, killing coccidia in all stages of intracellular development. It has a broad spectrum of insect resistance, and has a high curative effect on coccidia in chickens, geese and pigeons, and is highly effective against mild and severe coccidia infections. [0003] The synthetic method of toltrazuril has many bibliographical reports, and wherein comparatively having industrial value is to use 1-methyl-5-[3-methyl-4-(4-trifluoromethylthio-phenoxy)- Phenyl]-biuret (abbreviated as biuret hereinafter) is an intermediate, which carries out ring closure react...

Claims

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Application Information

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IPC IPC(8): C07C323/20C07C319/20C07D251/30
Inventor 刘聪蒋狄锋毛江南侯仲轲邱家军
Owner ZHEJIANG GUOBANG PHARMA
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