5-tetrazole-thione acetic acid and preparation method of sodium salt thereof

A technology of mercaptotetrazolium acetic acid disodium salt and mercaptotetrazolium acetic acid is applied in the field of preparation of 5-mercaptotetrazolium acetic acid and its sodium salt, and can solve the problems of toxicity, high raw material price, low yield and the like, To achieve the effect of reducing process costs

Active Publication Date: 2018-03-16
九江中星医药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a kind of preparation method of 5-mercaptotetrazolium acetic acid and its sodium salt, solve the low yield,

Method used

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  • 5-tetrazole-thione acetic acid and preparation method of sodium salt thereof

Examples

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Effect test

Embodiment 1

[0015] Embodiment 1: the preparation of 5-mercaptotetrazolium acetic acid

[0016] Add (71.5g, 1.1mol) sodium azide, (18.5g, 0.1mol) benzyltriethylammonium chloride, and 150mL water into a 500mL three-necked flask. In a nitrogen atmosphere, the temperature of the system was raised to 60° C. and kept stirring. (145.0 g, 1.0 mol) ethyl isothiocyanoacetate was slowly added dropwise to the system. After the drop was completed, the system was heated to 75° C. for 4 h. After the reaction, the temperature of the system was lowered to 5° C., and the pH of the system was adjusted to about 12 with 50% NaOH solution, and stirred for 0.5 h until the pH was stable. The temperature of the system was raised to 75°C, and the reaction was kept for 5 hours. After the reaction, the system was cooled to room temperature, and hydrochloric acid (150.0 g, wt%=31%) was slowly added to the system. After the addition, react at room temperature for 2h. The reaction system was extracted with (200 mL×...

Embodiment 2

[0018] Embodiment 2: Preparation of monosodium salt of 5-mercaptotetrazolium acetic acid

[0019] Add (100.0 g, 0.63 mol) 5-mercaptotetrazolium acetic acid and 150 mL of water into a 500 mL three-neck flask. The system was stirred at room temperature, and NaOH solution (250.0 g, wt% = 10%) was slowly added to the system, and the temperature of the system was raised to 90° C. for 2 hours after the addition. After the reaction was completed, the system was lowered to 10°C, filtered, and the filter cake was vacuum-dried at 60°C to obtain the product (104.0 g, 0.57 mol) of 5-mercaptotetrazolium acetic acid monosodium salt, with a yield of 90.0%.

Embodiment 3

[0020] Embodiment 3: Preparation of 5-mercaptotetrazolium acetic acid disodium salt

[0021] Add (100.0 g, 0.63 mol) 5-mercaptotetrazolium acetic acid and 150 mL of water into a 500 mL three-neck flask. The system was stirred at room temperature, and NaOH solution (500.0 g, wt% = 10%) was slowly added to the system, and the temperature of the system was raised to 90° C. for 2 hours after the addition. After the reaction was completed, the system was lowered to 10°C, filtered, and the filter cake was vacuum-dried at 60°C to obtain the product (117.0 g, 0.57 mol) of 5-mercaptotetrazolium acetic acid disodium salt with a yield of 90.0%.

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Abstract

The invention discloses a preparation method of 5-tetrazole-thione acetic acid. Sodium azide, benzyl trimethyl ammonium chloride and water are added into a three-mouth flask of 500mL, and ethyl acetate for an ethyl isothiocyanatoacetate reaction system is dropwise for extraction; organic phases are mixed, and a solvent is spin-dried to obtain a crude 5-tetrazole-thione acetic acid product; the obtained crude 5-tetrazole-thione acetic acid product is heated, dissolved and clarified, and activated carbon is added and stirred; a filter cake is subjected to vacuum drying to obtain the product 5-tetrazole-thione acetic acid. The preparation method has the advantages that a poisonous reagent methyl iodide is omitted in the synthesis of the 5-tetrazole-thione acetic acid and sodium salt thereof according to the above steps, the yield of the whole 5-tetrazole-thione acetic acid synthesis method is as high as 80%, and the single-step yield of the mono-sodium salt and disodium salt of the 5-tetrazole-thione acetic acid is as high as 90%. By adopting the method, the process cost is greatly reduced, and a feasible way is provided for industrialized production of the5-tetrazole-thione acetic acid.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of 5-mercaptotetrazolium acetic acid and its sodium salt. Background technique [0002] 5-Mercaptotetrazolium acetic acid and its salts are an important intermediate of cefrelide. The research on its synthesis method has aroused widespread concern. At present, its main synthesis method is provided by US4782012, and its route is as follows: [0003] [0004] The methyl iodide used in this route is an expensive toxic reagent and needs to be stored away from light. And this route product yield is low, is unfavorable for industrial scale-up production. Therefore, the problem to be solved by the present invention is to design a low-cost, environmentally friendly and suitable synthetic route for industrial production. Contents of the invention [0005] The object of the present invention is to provide a kind of preparation method of 5-mercaptotetrazolium ac...

Claims

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Application Information

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IPC IPC(8): C07D257/04
CPCC07D257/04
Inventor 周以鸿骆建轻程龙进张银生何文秀赖立冬
Owner 九江中星医药化工有限公司
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