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Compounding method for 2-thiopheneacetyl chloride

A technology of thiophene acetyl chloride and synthesis method, applied in directions such as organic chemistry, can solve the problems of noble iodide, unsuitable route for amplification, no simple operation, etc., and achieves the effects of easy availability of raw materials, concise route and mild reaction conditions

Active Publication Date: 2018-12-07
阜新孚隆宝医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0024] This route is too long and requires expensive iodide, so it is not suitable as a scale-up route
[0025] Based on the above various reaction routes, there is no relatively simple, safe and reliable process route suitable for industrial scale-up

Method used

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  • Compounding method for 2-thiopheneacetyl chloride
  • Compounding method for 2-thiopheneacetyl chloride
  • Compounding method for 2-thiopheneacetyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of ethyl 2-thiophene acetate:

[0044] Mix 20 grams of thiophene with 10 times the volume of dichloroethane, add 1.1 equivalents of ethyl glycolate and 1.1 equivalents of polyphosphoric acid, reflux for 4 hours, and cool to room temperature. The reaction solution was washed successively with cold water and saturated brine, dried and concentrated, and the obtained crude product was directly used for the next hydrolysis reaction.

[0045] Preparation of 2-thiopheneacetic acid:

[0046] Suspend the crude product obtained in the first step in 3 times the volume of ethanol, add 5 times the volume of 6N hydrochloric acid aqueous solution, reflux for 8 hours, cool to about 5°C, the product is directly precipitated, filtered, washed with water, and dried to obtain pure 2-thiopheneacetic acid. HPLC 99.2%, melting point 63-65°C.

[0047] Preparation of 2-thiopheneacetyl chloride:

[0048] Dissolve thiopheneacetic acid obtained in the second step in 10 times the vol...

Embodiment 2

[0050] Preparation of methyl 2-thiopheneacetate:

[0051] Mix 20 g of thiophene with 10 volumes of dichloroethane, add 1.1 equivalents of methyl glycolate and 1.1 equivalents of p-toluenesulfonic acid, reflux for 4 hours, and cool to room temperature. The reaction solution was washed successively with cold water and saturated brine, dried and concentrated, and the obtained crude product was directly used for the next hydrolysis reaction.

[0052] Preparation of 2-thiopheneacetic acid:

[0053] Suspend the crude product obtained in the first step in 3 times the volume of acetonitrile, add 5 times the volume of 6N hydrochloric acid aqueous solution, reflux for 8 hours, cool to about 5°C, the product is directly precipitated, filtered, washed with water, and dried to obtain pure 2-thiopheneacetic acid. HPLC 99.1%, melting point 63-65°C.

[0054] Preparation of 2-thiopheneacetyl chloride:

[0055] Dissolve thiopheneacetic acid obtained in the second step in 10 times the volume ...

Embodiment 3

[0057] Preparation of isopropyl 2-thiopheneacetate:

[0058] Mix 20 g of thiophene with 10 times the volume of dichloroethane, add 1.1 equivalents of isopropyl glycolate and 1.1 equivalents of p-toluenesulfonic acid, reflux for 4 hours, and cool to room temperature. The reaction solution was washed successively with cold water and saturated brine, dried and concentrated, and the obtained crude product was directly used for the next hydrolysis reaction.

[0059] Preparation of 2-thiopheneacetic acid:

[0060] Suspend the crude product obtained in the first step in 3 times the volume of acetonitrile, add 5 times the volume of 6N hydrochloric acid aqueous solution, reflux for 10 hours, cool to about 20°C, the product is directly precipitated, filtered, washed with water, and dried to obtain pure 2-thiopheneacetic acid. HPLC 99.1%, melting point 63-65°C.

[0061] Preparation of 2-thiopheneacetyl chloride:

[0062] Same as Example 1.

[0063] The total yield of the three steps ...

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Abstract

The invention discloses a compounding method for 2-thiopheneacetyl chloride and belongs to the technical field of organic synthesis. The 2-thiopheneacetyl chloride is compounded by taking thiophene asa raw material through following three-step reaction: 1) acquiring 2-thiophene acetate through the F-C reaction of thiophene and glycolate under the existence of catalyst; 2) hydrolyzing the 2-thiophene acetate under the existence of acid, thereby acquiring 2-thiopheneacetic acid; 3) treating the 2-thiopheneacetic acid in the manner of acylating chlorination with thionyl chloride under the catalysis of pyridine, thereby acquiring 2-thiopheneacetyl chloride. The compounding method for 2-thiopheneacetyl chloride has the characteristics of easily acquired raw materials and simple and convenientoperation and is suitable for industrial production.

Description

technical field [0001] The invention relates to the preparation of acid chloride compounds, in particular to a preparation method of 2-thiopheneacetyl chloride, which belongs to the technical field of organic synthesis of pharmaceutical and chemical intermediates. 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. The structural modification of the cephalosporin mother nucleus can improve the antibacterial activity of the drug. In addition, 2-thiopheneacetyl chloride is also widely used in the fields of pesticides, dyes and other fine chemicals. [0003] In the synthetic method of 2-thiophene acetyl chloride, thiophene is mostly used as a raw material, and a multi-step synthesis process is adopted to finally obtain the target product. The main reaction routes are as follows: [0004] Route 1: British Pat No.1122658 reported...

Claims

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Application Information

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IPC IPC(8): C07D333/24
CPCC07D333/24
Inventor 蔡凡平李新明
Owner 阜新孚隆宝医药科技有限公司
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