Synthetic method of aminothiazoly loximate

A technology of aminothiaxamic acid and synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of long production cycle, excessive waste water, high production cost, etc., achieve the effects of reducing the discharge of three wastes, simplifying the operation process, and reducing production costs

Inactive Publication Date: 2013-04-03
YIYUAN XINQUAN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] (1) The production cycle is long, the intermediate products in the production process are not easy to detect, the use of production equipment is high, the production cost is high, and the production produces a lot of waste water and three wastes
[0008] (2) The process of nitrosation reaction is a heterogeneous reaction, not only the reaction speed is slow, resulting in a long period, but also the yield is low
[0009] (3) Chlorine gas is used as the chlorination agent in the chlorination process, the reaction is not easy to control, and its toxicity is high, posing safety hazards

Method used

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  • Synthetic method of aminothiazoly loximate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1) Add 60mL of ethanol aqueous solution (volume ratio 1:2), 20mL of ethyl acetoacetate, and 11g of ethyl nitrite into a three-necked flask, stir, and add 25g of glacial acetic acid dropwise at a temperature of 5±3°C. Continue to stir and react for 2h after completion; pass into N after completion of the reaction 2 1h, then add 0.4g tetrabutylammonium iodide, start to drop 20mL of dimethyl sulfate, control the temperature at 11±3°C, pH value is 8, react for 2h; dissolve 10g of triphosgene in 20mL of chloroform and add 0.5mL of DMF, Make a triphosgene solution, after the reaction is completed, slowly add the prepared triphosgene solution, control the reaction temperature at 15±3°C, and react for 2 hours; after the reaction is completed, add 10mL of ethanol aqueous solution, add 8g of thiourea, 16g of sodium acetate and 0.5g Tetrabutylammonium iodide, the reaction temperature is controlled at 30±3°C, the dropwise addition time is 1.5h, the dropwise temperature is kept for...

Embodiment 2

[0041] (1) Add 60mL of ethanol aqueous solution (volume ratio 1:2), 20mL of ethyl acetoacetate, and 11g of methyl nitrite into a three-necked flask, stir, and add 48g of glacial acetic acid dropwise at a temperature of 3±3°C. Continue to stir and react for 2h after completion; pass into N after completion of the reaction 2 1h, then add 0.6g of benzyltriethylammonium bromide, start to drop 20mL of dimethyl sulfate, control the temperature at 12±3℃, pH value is 9, react for 3h; dissolve 10g of triphosgene in 20mL of chloroform and add 0.5 Prepare triphosgene solution in mL of triethylamine. After the reaction is completed, slowly add the prepared triphosgene solution, control the reaction temperature at 16±3°C, and react for 2.5 hours; 16g sodium acetate and 0.7g benzyltriethylammonium bromide, control the reaction temperature at 27±3°C, add dropwise for 1.5h, keep the temperature for 2h after dropping, adjust the pH value to 7.4 with sodium carbonate solution, and cool down to ...

Embodiment 3

[0047] (1) Add 60mL ethanol aqueous solution (volume ratio 1:2), 20mL ethyl acetoacetate, and 13g n-propyl nitrite into a three-necked flask, stir at a temperature of 5±3°C, add 40g of glacial acetic acid dropwise, and finish adding in 1 hour. After the addition, continue to stir the reaction for 2h; after the reaction is completed, feed N 2 1h, then add 0.8g hexadecyltrimethylammonium bromide, start to drop 20mL of dimethyl sulfate, control the temperature at 9±3℃, pH value is 8~10, react for 4h; dissolve 10g triphosgene in 20mL Chloroform and add 0.5mL DMF to make a triphosgene solution. After the reaction is completed, slowly add the prepared triphosgene solution, control the reaction temperature at 14±3°C, and react for 2.5h; after the reaction is completed, add 10mL of ethanol aqueous solution and 8g of thiourea , 16g of sodium acetate and 0.9g of cetyltrimethylammonium bromide, control the reaction temperature at 33±3°C, dropwise adding time is 1.5h, keep warm for 2h aft...

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Abstract

The invention relates to a synthetic method of aminothiazoly loximate, which belongs to the synthetic method of a heterocyclic compound containing 1,3-thiazole ring, and in particular relates to a preparation method of the heterocyclic compound with two double bonds between the annular atoms and without other condensed rings. The method comprises the steps of: (1) using ethyl acetoacetate as a raw material, oximating, alkylating and cyclizing in a same reaction container to obtain ethyl methoxyiminoacetate; (2) modifying a nitrosation reagent in an oximation agent into organic nitrous acid ester by inorganic salt sodium nitrite, wherein organic nitrous acid ester is more suitable for the solvent system and the nitrosation effect is better; (3) hydrolysis: preparing an aminothiazoly loximate coarse product; and (4) refining: preparing an aminothiazoly loximate product. According to the process, the operating process of the reaction is simplified, the production cost is lowered, and the emission of three wastes is reduced. A triphosgene chlorinating agent which is smaller in toxicity, safe and convenient to use, easy to control and operate and high in yield is provided. Aminothiazoly loximate is a raw material for synthesizing third generation cephalosporin, and is an important medical intermediate.

Description

technical field [0001] The invention relates to a method for synthesizing aminothiaxamic acid, which belongs to a method for synthesizing heterocyclic compounds containing 1,3 thiazole rings, in particular to a method for preparing heterocyclic compounds containing two double bonds between ring atoms without other condensed rings. Background technique [0002] The chemical name of aminothioxamic acid is 2-methoxyimino-2-(2-aminothiazole)-4-acetic acid, the English name is 2-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acid, and the structural formula is: [0003] [0004] Aminothioxamic acid is an important pharmaceutical intermediate and a raw material for the synthesis of third-generation cephalosporins. Cephalosporin antibiotics have a good curative effect on infections caused by some drug-resistant bacteria and difficult-to-control pathogenic bacteria, and have low toxicity, broad-spectrum and long-acting effect, and their curative effect is dozens of times higher than...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/593
Inventor 唐锋段会伟
Owner YIYUAN XINQUAN CHEM
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