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Synthesis method of 2-thiophene acetylchloride

A technology of thiophene acetyl chloride and a synthesis method, which is applied in the field of preparation of 2-thiophene acetyl chloride, can solve the problems of cumbersome reaction steps, high cost, unsuitable for industrialized production and the like, and achieves high product purity, simple and convenient operation, and easy-to-obtain raw materials. Effect

Active Publication Date: 2010-11-10
LIANYUNGANG DIPU CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction steps of this method are cumbersome, the separation of intermediate products is difficult, and the yield of the target compound is low, so it is not suitable for industrial production.
Chinese patent application 200510047449 discloses a method for synthesizing 2-thiopheneacetic acid from thiophene and glyoxylic acid. Although the process is simple, the glyoxylic acid used needs to be dehydrated and the cost is high, and the excessive red Phosphorus for clarification

Method used

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  • Synthesis method of 2-thiophene acetylchloride

Examples

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Embodiment 1

[0030] Example 1. A kind of synthetic method of 2-thiophene acetyl chloride, its step is as follows:

[0031] (1) Preparation of 2-acetylthiophene: in the presence of a catalyst, thiophene and acylating agent were heated and reacted in an organic solvent for 3 hours, the molar ratio of thiophene and acylating agent was 1: 1.0, and the reaction temperature was 65° C. Collect 102 DEG C (15mmHg) fractions by vacuum distillation to obtain 2-acetylthiophene; the acylating agent is acetic acid; the catalyst used is concentrated phosphoric acid; the organic solvent is ethylene dichloride;

[0032] (2) Preparation of 2-thiophene glyoxylic acid: in the presence of catalyst, get 2-acetylthiophene and carry out heating reaction in the mixed solution of sodium nitrite and hydrochloric acid, the weight ratio of 2-acetylthiophene, sodium nitrite and hydrochloric acid is 1:1.5:10, the reaction temperature is 65°C, cool down after the reaction, adjust the pH to 2, extract with organic solven...

Embodiment 2

[0035] Example 2. A kind of synthetic method of 2-thiophene acetyl chloride, its step is as follows:

[0036] (1) Preparation of 2-acetylthiophene: in the presence of a catalyst, thiophene and acylating agent were heated and reacted in an organic solvent for 10 hours, the molar ratio of thiophene and acylating agent was 1: 1.8, and the reaction temperature was 95° C. Collect 105 DEG C (15mmHg) fractions by vacuum distillation to obtain 2-acetylthiophene; the acylating agent is acetyl chloride; the catalyst used is molecular sieve; the organic solvent is tetrachloroethylene;

[0037] (2) Preparation of 2-thiophene glyoxylic acid: in the presence of catalyst, get 2-acetylthiophene and carry out heating reaction in the mixed solution of sodium nitrite and hydrochloric acid, the weight ratio of 2-acetylthiophene, sodium nitrite and hydrochloric acid is 1:5.0:15, the reaction temperature is 95°C, cool down after the reaction, adjust the pH to 3, extract with organic solvent to rem...

Embodiment 3

[0040] Example 3. A kind of synthetic method of 2-thiophene acetyl chloride, its step is as follows:

[0041] (1) Preparation of 2-acetylthiophene: in the presence of a catalyst, thiophene and acylating agent were heated and reacted in an organic solvent for 6 hours, the molar ratio of thiophene and acylating agent was 1: 1.2, and the reaction temperature was 85° C. Vacuum distillation collects fractions at 103°C (15mmHg) to obtain 2-acetylthiophene; the acylating agent is acetic anhydride; the catalyst used is trifluoromethanesulfonate; the organic solvent is N,N-dimethylformaldehyde amides;

[0042] (2) Preparation of 2-thiophene glyoxylic acid: in the presence of catalyst, get 2-acetylthiophene and carry out heating reaction in the mixed solution of sodium nitrite and hydrochloric acid, the weight ratio of 2-acetylthiophene, sodium nitrite and hydrochloric acid is 1:3:13, the reaction temperature is 85°C, cool down after the reaction, adjust the pH to 3, extract with orga...

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Abstract

The invention relates to a synthesis method of 2-thiophene acetylchloride. The method is characterized by using thiophene as a raw material and mainly comprising the following steps of: (1) acetylating the thiophene in the presence of a catalyst to obtain 2-acetyl thiophene; (2) acting the 2-acetyl thiophene with sodium nitrite and hydrochloric acid in the presence of a catalyst to obtain 2-thiophene glyoxylic acid; (3) reducing the 2-thiophene glyoxylic acid by using hydrazine hydrate to obtain 2-thiopheneacetic acid; and (4) acyl chloridizing the 2-thiopheneacetic acid to obtain the 2-thiophene acetylchloride. The synthesis method has the advantages of easy obtaining of raw materials, simple and convenient operation, high yield, high product purity, and the like and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 2-thiopheneacetyl chloride, which belongs to the technical fields of medicine and chemical industry. Background technique [0002] 2-thiophene acetyl chloride is widely used in the pharmaceutical industry. It is an intermediate of broad-spectrum antibacterial drugs cephalothin, cefotaxime, and cefoxitin. It can modify the structure of cephalosporin core 7-aminocephalosporanic acid (7-ACA) , can improve the antibacterial activity of the drug. In recent years, many new cephalosporin antibiotics have been developed by using 2-thiophene acetyl chloride abroad, including ceftriazole, cefniterol and furonicazone. In addition, 2-thiophene acetyl chloride is also widely used in the fields of pesticides, dyes and other fine chemicals. [0003] There are many methods reported about the synthesis of 2-thiophene acetyl chloride, and these methods all use thiophene as a raw material and adopt a multi-step synthesis...

Claims

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Application Information

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IPC IPC(8): C07D333/24
Inventor 付瑞新龙得安
Owner LIANYUNGANG DIPU CHEM
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