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Preparation method of 3-thiophenecarboxaldehyde

A thiophene formaldehyde, methyl thiophene technology, applied in the direction of organic chemistry, can solve the problems of high equipment and temperature requirements, difficult industrial production, high cost, and achieve the effects of avoiding pollution, simple operation, and saving raw material costs.

Inactive Publication Date: 2020-03-13
NANJING JIEYUN PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The main purpose of the present invention is to overcome the defects in the existing preparation method of 3-thiophene carboxaldehyde, and provide a new preparation method of 3-thiophene carboxaldehyde, which can effectively solve the problems existing in the existing preparation method. High equipment and temperature requirements, high energy consumption, high cost, and difficulty in industrial production

Method used

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  • Preparation method of 3-thiophenecarboxaldehyde
  • Preparation method of 3-thiophenecarboxaldehyde
  • Preparation method of 3-thiophenecarboxaldehyde

Examples

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preparation example Construction

[0035] The preparation method as described herein is carried out according to the following reaction equation:

[0036]

[0037] in,

[0038] 1: Mix 3-methylthiophene and an organic solvent and heat to the first temperature, keep the first temperature constant, add azobisisobutyrocyanide and N-halogenated succinimide respectively, in the After being kept warm for a period of time at the first temperature, the temperature is lowered, and then filtered to obtain a mixed solution of 3-halomethylthiophene;

[0039] 2: Add N-methylmorpholine-N-oxide to the mixed solution of 3-halomethylthiophene obtained above, heat it to the second temperature, then cool down, wash with water, and remove the solvent to obtain the crude product, and further rectify , that is, the pure product of 3-thiophenecarbaldehyde is obtained.

[0040] Specifically as described in the following examples.

Embodiment 1

[0042] Add 35.2g of 3-methylthiophene and 206g of ethyl acetate to the three-necked flask, heat the system to 70°C, then add 11.71g of azobisisobutyrocyanide and 45.23g of N-chlorosuccinyl in batches at this temperature For imine (NCS), after the addition was completed, the temperature was lowered at 70°C for 2 hours, and the precipitated solid was removed by filtration to obtain an ethyl acetate solution of 3-chloromethylthiophene.

[0043]Add 125.3 g of NMO solid (N-methylmorpholine-N-oxide) to the above ethyl acetate solution of 3-chloromethylthiophene, and heat the system to 50°C for 6 hours. Washing with water and precipitation to obtain 23.6 g of 3-thiophenecarbaldehyde with a yield of 58.69%, and further rectification to obtain pure 3-thiophenecarbaldehyde.

Embodiment 2

[0045] Add 37.6g of 3-methylthiophene and 231g of ethyl acetate to the three-necked flask, heat the system to 70°C, then add 12.58g of azobisisobutyrocyanide and 64.76g of N-bromobutylene in batches at this temperature Imide (NBS), after the addition of imide (NBS), the temperature was lowered at 70°C for 2 hours, and the precipitated solid was removed by filtration to obtain an ethyl acetate solution of 3-bromomethylthiophene.

[0046] Add 134.61 g of NMO solid (N-methylmorpholine-N-oxide) to the ethyl acetate solution of the above-mentioned 3-bromomethylthiophene, and heat the system to 50°C for 6 hours. Washing with water and solvent removal gave 26.7 g of 3-thiophenecarbaldehyde with a yield of 62.16%. Further rectification gave pure 3-thiophenecarbaldehyde.

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Abstract

The invention discloses a preparation method of 3-thiophenecarboxaldehyde. The preparation method comprises the following steps: mixing and heating 3-methylthiophene and an organic solvent to a firsttemperature, keeping the first temperature unchanged, respectively adding azobisisobutyronitrile and N-halogenated succinimide, carrying out heat insulation at the first temperature for a period of time, cooling the obtained solution, and filtering the cooled solution to obtain a mixed solution of 3-halogenated methylthiophene; adding N-methylmorpholine-N-oxide into the mixed solution of 3-halogenated methylthiophene without any treatment, heating the obtained solution to a second temperature, cooling the obtained solution, washing the cooled solution with water, desolventizing the cooled solution to obtain a crude product, and further rectifying the crude product to obtain the pure 3-thiophenecarboxaldehyde product. The method solves the problems of poor selectivity, low yield and the like of existing synthesis methods, and is a high-selectivity and high-yield method for synthesizing the 3-thiophenecarboxaldehyde under mild reaction conditions; and the preparation method has the advantages of simplicity in operation, no irritation, easily available raw materials, and saving of the operation cost and the raw material cost, and is suitable for industrial production of 3-thiophenecarboxaldehyde.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 3-thiophenecarbaldehyde. Background technique [0002] 3-Thiophenecarbaldehyde is a colorless or light yellow liquid. The color of the solution gradually becomes darker when exposed to light, and it has a pungent odor. It is easily soluble in organic solvents such as alcohol, benzene, ether, and methylene chloride, and slightly soluble in water. 3-thiophene carboxaldehyde is an important pharmaceutical intermediate, mainly used in amine antibacterial and anti-inflammatory drugs for the treatment of infections caused by staphylococcus, streptococcus, pneumococcus and meningococcus. At present, the new anti-HIV drug newly developed by Pfizer requires a large amount of 3-thiophene carboxaldehyde as the starting material, but the research and development of 3-thiophene carboxaldehyde in my country is insufficient, and the production capacity is small...

Claims

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Application Information

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IPC IPC(8): C07D333/22
CPCC07D333/22
Inventor 宋兴昌方靖舒恺周禾张力余增辉吴晓东刘郝敏
Owner NANJING JIEYUN PHARMA TECH CO LTD
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