Guanoxan sulfate synthesis method

A technology of guanidine sulfate production and synthesis method, which is applied in the field of organic drug synthesis, can solve the problems of high toxicity of 1,2-epichlorohydrin, influence the market competitiveness of products, and many synthesis steps, and achieves low toxicity and short synthesis route. , the effect of simple synthesis steps

Active Publication Date: 2015-11-18
SHANGHAI MODERN HASEN SHANGQIU PHARMA
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  • Application Information

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Problems solved by technology

[0006] The above-mentioned synthesis techniques mostly have the following disadvantages: many synthesis steps, complex operation, low yield, and the toxicity of the raw material 1,2-epichlorohydrin used is relatively high. These factors all affect the market competitiveness of the product and need to be further improved.

Method used

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Embodiment 1

[0023] A kind of guanidine sulfate synthetic method, it comprises the steps:

[0024] 1) Synthesis of 2-hydroxymethyl-1,4-benzodioxane:

[0025] Add 20g (182mmol) of ortho-catechol, 80g of water and 39.6g (990mmol) of sodium hydroxide into the reaction bottle, protect it with nitrogen, heat (about 70-80°C) and stir to dissolve, then add 30ml of toluene, stir slowly 29.5 g (200 mmol) of 1,2,3-trichloropropane was added dropwise, and after the dropwise addition was completed, the temperature was raised and refluxed for reaction for 3.5 hours. After the reaction, cool down to below 15°C, separate the organic layer, extract the water layer twice with toluene (20ml*2), combine the toluene layer, wash with water, evaporate the toluene under reduced pressure, add 50ml of water to the residue, heat to dissolve and cool down to 15°C Below ℃, crystals were precipitated, filtered, and dried to obtain 25.0 g of solid 2-hydroxymethyl-1,4-benzodioxane, with a yield of 82%.

[0026] 2) Syn...

Embodiment 2

[0031] A kind of guanidine sulfate synthetic method, it comprises the steps:

[0032] 1) Synthesis of 2-hydroxymethyl-1,4-benzodioxane:

[0033] Add 20g (182mmol) of ortho-catechol, 80g of water and 51g (910mmol) of potassium hydroxide into the reaction bottle, protect with nitrogen, heat (about 70-80°C) and stir to dissolve, then add 30ml of toluene, slowly drop under stirring 29.5 g (200 mmol) of 1,2,3-trichloropropane was added, and after the dropwise addition was completed, the temperature was raised to reflux for 3.5 hours. After the reaction, cool down to below 15°C, separate the organic layer, extract the water layer twice with toluene (20ml*2), combine the toluene layer, wash with water, evaporate the toluene under reduced pressure, add 50ml of water to the residue, heat to dissolve and cool down to 15°C Below ℃, crystals were precipitated, filtered, and dried to obtain 25.7 g of solid 2-hydroxymethyl-1,4-benzodioxane, with a yield of 85%.

[0034] 2) Synthesis of 2-...

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Abstract

The invention belongs to the technical field of organic drug synthesis, and particularly relates to a guanoxan sulfate synthesis method. The method comprises steps as follows: 1), 2-hydroxymethyl-1,4-benzodioxane and thionyl chloride have a chlorination reaction under the condition of existence of a solvent I, and 2-chloromethyl-1,4-benzodioxane is obtained; 2), 2-chloromethyl-1,4-benzodioxane and guanidine are condensed under the condition of existence of alkali and a solvent II, guanoxan is obtained, guanoxan and sulfuric acid are salified, and a finished product guanoxan sulfate is obtained. According to the guanoxan sulfate synthesis method, technological synthesis steps are simple, a route is short, raw material toxicity is relatively lower, and the yield and the purity of the product are high.

Description

technical field [0001] The invention belongs to the technical field of organic medicine synthesis, and in particular relates to a synthesis method of guanidine sulfate. Background technique [0002] Guanidine sulfate, chemical name: 2-guanidinium methyl-1,4-benzodioxane sulfate, also known as guanidine axan, is a powerful antihypertensive drug, and its mechanism of action is to prevent the action of norepinephrine Normal release, weakening vasoconstriction, used for essential hypertension, severe and moderate to severe renal and malignant hypertension, this product is white crystalline powder, odorless, soluble in ethanol, soluble in water, insoluble in chloroform and ether. [0003] The synthetic method of the guanidine sulfate that has been reported at present mainly contains: the synthetic method that 470 pages of collection of pharmaceutical technology collects, or the 5th page of the 4th phase of the 14th volume of Shandong Pharmaceutical Industry Journal in 1995, or t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/20
CPCC07D319/20
Inventor 王英利陈洪江正祥张哲刁文瑞翟宝琪刘砺
Owner SHANGHAI MODERN HASEN SHANGQIU PHARMA
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