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A method for synthesizing 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione

A technology of isothiocyanatonaphthalene and cyclopropyl, which is applied in the field of synthesis of 1-cyclopropyl-4-isothiocyanatonaphthalene, can solve the problem of high cost, complex process, prolongation of 1-cyclopropyl-4- Problems such as the synthesis route of isothiocyanatonaphthalene, to achieve the effects of reducing the amount of production, simple reaction process, stable reaction and easy control

Inactive Publication Date: 2015-04-22
ANHUI WANBANG MEDICAL TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] This route avoids the use of thiophosgene, but this method greatly prolongs the synthetic route of 1-cyclopropyl-4-isothiocyanatonaphthalene, making the process more complicated and costly

Method used

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  • A method for synthesizing 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione
  • A method for synthesizing 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione
  • A method for synthesizing 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 100 mL of toluene, 18.3 g (0.100 mol) of 4-cyclopropyl-1-naphthylamine, and 33.7 g (0.3 mol) of triethylenediamine into a 250 mL three-necked flask, and stir at room temperature. Add 22.8 g (0.300 mol) of carbon disulfide dropwise, and stir at room temperature for 4-10 hours after the addition, and a large amount of solids precipitate out. After suction filtration and drying, 33.5 g of 4-cyclopropyl-1-naphthylaminodithioformic acid triethylenediamine salt was obtained, with a yield of 90.1%;

[0028] Add 33.5g (0.090 mol) of the solid product from the previous step reaction into three 250mL flasks, add 100mL of chloroform, stir and cool down to 5~10°C, slowly add 9.9 g (0.033mol) of BTC in chloroform solution dropwise, after the addition is complete The reaction was stirred at room temperature for 1 hour, and after the reaction was completed, the temperature was raised to 40-65° C. for reflux reaction for 1 hour. After cooling to room temperature, the insoluble mat...

Embodiment 2

[0030] Add 100 mL of xylene, 18.3 g (0.100 mol) of 4-cyclopropyl-1-naphthylamine, and 30.4 g (0.300 mol) of triethylamine into a 250 mL three-necked flask, and stir at room temperature. 22.8 g (0.300 mol) of carbon disulfide was added dropwise, and stirred at room temperature for 4-10 hours after the addition was complete, a large amount of solids precipitated. After suction filtration and drying, 31.8 g of 4-cyclopropyl-1-naphthylaminodithioformic acid triethylamine salt was obtained, with a yield of 88.2%;

[0031] Add 31.8 g (0.088 mol) of the solid product from the previous step reaction into three 250 mL flasks, add 100 mL of dichloromethane, stir and cool down to 5~10°C, slowly add 9.9 g (0.033 mol) of BTC in chloroform solution dropwise, add After the completion, the reaction was stirred at room temperature for 1 hour, and after the reaction was completed, the temperature was raised to 40-65° C. for reflux reaction for 3 hours. After cooling to room temperature, the in...

Embodiment 3

[0033] Add 100 mL of xylene, 18.3 g (0.100 mol) of 4-cyclopropyl-1-naphthylamine, and 23.7 g (0.300 mol) of pyridine into a 250 mL three-necked flask, and stir at room temperature. 22.8 g (0.300 mol) of carbon disulfide was added dropwise, and stirred at room temperature for 4-10 hours after the addition was complete, a large amount of solids precipitated. After suction filtration and drying, 29.5 g of 4-cyclopropyl-1-naphthylaminopyridinium dithiocarbamate was obtained, with a yield of 87.1%;

[0034] Add 29.5 g (0.087 mol) of the solid product of the previous step reaction into three 250 mL flasks, add 100 mL of chloroform, stir and cool down to 5~10°C, slowly add dichloromethane dissolved in 9.8 g (0.090 mol) of ethyl chloroformate After the addition of the solution, stir and react at room temperature for 1 hour, and then heat up to 40~65°C for reflux for 3 hours after the reaction. After cooling to room temperature, the insoluble matter was removed by suction filtration, ...

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Abstract

The present invention discloses a method for synthesizing 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione. The method includes the following steps: using 4-cyclopropyl-1-naphthylamine (formula A) as a starting reactant, reacting the formula A with carbon disulfide to generate 4-cyclopropyl-1-naphthylamino dithiocarbamate (formula B) under a organic alkaline condition, reacting the formula B with bis (trichloromethyl) carbonate (BTC) or acylating reagents like ethyl chloroformate and methyl chloroformate, etc. to generate 4-cyclopropyl-1-naphthylamino dithiocarbamate chloro-carbonic acid anhydride, conducting decomposition reaction to the resulting product without separation and purification to produce 4-cyclopropyl-1-naphthyl isothiocyanate. The method uses carbon disulfide instead of thiophosgene with greater toxicity, and provides simple process and stable reaction. Furthermore, raw materials are readily available, and industrialization is easy to be realized with a total recovery of more than 65%.

Description

technical field [0001] The present invention relates to a kind of synthetic method of known compound, more specifically relate to a kind of synthetic method of 1-cyclopropyl-4-isothiocyanatonaphthalene. Background technique [0002] 1-Cyclopropyl-4-isothiocyanatonaphthalene is an important intermediate of the anti-gout drug Lesinurad. Lesinurad is a new type of anti-gout drug developed by Yade Biochemical Company in the United States. Naphthalene can be easily obtained from Lesinurad (refer to patent US0197825), and the reaction formula is as follows: [0003] [0004] The preparation methods of 1-cyclopropyl-4-isothiocyanatonaphthalene reported at present are relatively few. In addition to patent US0197825 reporting its synthesis, patents WO2009070740A2, US2010056464A1, WO2011085009A2, etc. also report the synthesis process of the anti-gout drug Lesinurad. The synthesis of the intermediate 1-cyclopropyl-4-isothiocyanatonaphthalene is mentioned: [0005] [0006] Thi...

Claims

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Application Information

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IPC IPC(8): C07C331/28
Inventor 陈国祥陶春蕾易加明李杰杨欣怡邵凤
Owner ANHUI WANBANG MEDICAL TECH
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