Method for synthesizing analgin

A technology of analgin and methylamphenicol, which is applied in the field of compound synthesis, can solve the problems of long synthesis route, many by-products and high cost, and achieve the effects of short production cycle, pollution reduction and quality assurance.

Active Publication Date: 2013-12-18
WUHAN WUYAO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis route is long, the cost is high, the by-products are many, the energy consumption is high, and a large amount of industrial wastes that are difficult to handle will also be produced during the synthesis process. Therefore, finding a more economical synthesis method has great economic and social benefits

Method used

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  • Method for synthesizing analgin
  • Method for synthesizing analgin
  • Method for synthesizing analgin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Preparation of 4-N-desmethyl Sulpyrine

[0048] 20.3 g of 4-aminoantipyrine (AA) (0.1 mol), 10.4 g of sodium bisulfite (0.1 mol), 3 g of paraformaldehyde (0.1 mol) and 100 ml of 95% ethanol were added to a 250 ml reaction bottle, stirred and heated to reflux for 1 hour. After the reaction liquid was lowered to 45°C, solid 4-N-desmethyl sulpyrine was added to the reaction liquid to cause crystallization. After vigorously stirring for half an hour, the solid was collected by filtration to obtain 30.3 g of 4-N-desmethyl sulpyrine. The rate is 90%; melting point: 217°C; 1 H NMR (400MHz, DMSO-d 6 )δ: 2.18(s, 3H), 2.80(s, 3H), 3.78(d, J=6.96Hz, 2H), 4.00(m, 1H), 7.25(m, 1H), 7.45(m, 4H); 13 C NMR (100MHz, DMSO-d 6 )δ: 161.8, 140.8, 135.4, 128.9(2), 125.3, 122.1(2), 120.0, 62.4, 37.7, 10.4.

Embodiment 2

[0049] Embodiment 2 Preparation of Sulpyrine

[0050] 33 grams of 4-N-desmethyl sulpyrine (0.1mol) were dissolved in 100 milliliters of 95% ethanol, and 16.5 grams of dimethyl sulfate (0.13mol) and 10.4 grams of sodium bicarbonate (0.13mol) were added successively, and stirred And heated to 60 ° C for 1 hour. The reaction solution was neutralized with acetic acid to pH 7-8, stirred and cooled, and then crystallized. The solid was collected by filtration to obtain 31 g of Sulpyrine with a yield of 89%; the purity determined by HPLC was 99.5%.

Embodiment 3

[0051] Embodiment 3 The preparation of Sulpyrine (one-pot method)

[0052] 20.3 g of 4-aminoantipyrine (AA) (0.1 mol), 10.4 g of sodium bisulfite (0.1 mol), 3 g of paraformaldehyde (0.1 mol) and 100 ml of 95% ethanol were added to a 250 ml reaction bottle, stirred and heated to reflux for 1 hour. The reaction solution was stirred and cooled to 40° C., then 16.5 g of dimethyl sulfate (0.13 mol) and 10.4 g of sodium bicarbonate (0.13 mol) were sequentially added, stirred and heated to 60° C. for 1 hour. The reaction solution was neutralized with acetic acid to pH 7-8, stirred and cooled, and then crystallized. The solid was collected by filtration to obtain 26 g of Sulpyrine with a yield of 74%. The purity determined by HPLC was 99.3%.

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Abstract

The invention relates to a new production process for an analgesic-antipyretic analgin. In the conventional synthesis route for the analgin, 4-aminoantipyrine (AA) is prepared into the analgin through four reactions, namely formylation, methylation, hydrolysis and condensation, while in the new method, the 4-aminoantipyrine (AA), paraformaldehyde and sodium hydrosulfite are directly subjected to condensation to form 4-N-demethylanalgin, and the 4-N-demethylanalgin and dimethyl sulfate are subjected to methylation under weak alkaline condition to form the analgin. By the process, the original four reactions are reduced to two reactions, the operation is greatly simplified, the cost is reduced, and three wastes are reduced.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a new synthesis method of analgin, an antipyretic and analgesic drug. Background technique [0002] Analgin belongs to antipyretic and analgesic and non-steroidal anti-inflammatory analgesic drugs. It has been on the market for 100 years. It has definite curative effect, convenient use, various dosage forms and low price. It has played an important role in clinical medicine for many years. . It has a wide market in many countries in the world, especially in developing countries, where it is widely used and in great demand. It is mainly used to reduce fever, but also to treat acute arthritis, headache, rheumatic pain, toothache and muscle pain. Because it is easy to cause adverse reactions, it is generally not the first-choice drug at present, and it is only used for emergency fever reduction in cases of acute high fever and severe illness, and no other ef...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/48
Inventor 杨尚金董建强魏金维谢国范
Owner WUHAN WUYAO PHARMA
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