A kind of preparation method of 3-thiophene formaldehyde

A technology of thiophene formaldehyde and tetramethoxypropane, applied in the direction of organic chemistry and the like, can solve the problems of low reagent safety, low reaction temperature, difficult to enlarge, etc., and achieves saving operating cost and energy consumption, high yield, and reduction of raw materials. cost effect

Active Publication Date: 2019-08-06
济南尚博医药股份有限公司
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Problems solved by technology

[0005] The object of the present invention is to provide a kind of preparation method that is applicable to industrialized production 3-thiophene formaldehyde, simple and economical to operate, high yield, high purity, to solve the very low reaction temperature that exists in the prior art, reagent safety is low and Technical issues that are not easily magnified

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  • A kind of preparation method of 3-thiophene formaldehyde
  • A kind of preparation method of 3-thiophene formaldehyde
  • A kind of preparation method of 3-thiophene formaldehyde

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preparation example Construction

[0039] The preparation method of 3-thiophenecarbaldehyde of the present invention, comprises the steps:

[0040] (a) Adding acid to 1,1,3,3-tetramethoxypropane under stirring conditions, controlling the reaction temperature to 20-40°C, and stirring for 2-3 hours;

[0041] (b) adding 1,4-dithio-2,5-diol and a base to the mixture obtained in step (a), controlling the reaction temperature to 50-70° C., and reacting for 4-6 hours to obtain a 3-thiophene formaldehyde solution;

[0042] (c) Post-treat the 3-thiophene formaldehyde solution to obtain 3-thiophene formaldehyde; specifically, add the 3-thiophene formaldehyde solution into water to quench, then add an organic solvent to extract and separate the organic phase, wash the organic phase with water, and concentrate to obtain the obtained 3-thiophenecarbaldehyde.

[0043] Wherein, the molar ratio of the 1,4-dithio-2,5-diol, 1,1,3,3-tetramethoxypropane, acid and base is preferably 1:(2-4):(0.2 -0.4): (0.5-1). Within this ratio...

Embodiment 1

[0051] The preparation method of the 3-thiophenecarbaldehyde of present embodiment, comprises the steps:

[0052] (a) Add 2mol of 1,1,3,3-tetramethoxypropane to the reaction vessel at room temperature, and add 0.2mol of hydrochloric acid with a mass fraction of 10% under stirring conditions (0.2mol refers to the addition of hydrochloric acid The amount of HCl, the following examples are the same), the reaction temperature is controlled at 20°C, and the reaction is stirred for 2h.

[0053] (b) Add 1 mol of 1,4-dithio-2,5-diol and 0.5 mol of triethylamine to the mixture in the reaction vessel in step (a), control the reaction temperature to 60°C, and stir for 4 hours , to obtain 3-thiophene formaldehyde solution.

[0054] (c) Add the 3-thiophene formaldehyde solution obtained in step (b) dropwise to cold water at 5°C to quench, after the dropwise addition, add ethyl acetate to the system for extraction and phase separation, and collect the organic phase; Add water to wash with...

Embodiment 2

[0056] The preparation method of the 3-thiophenecarbaldehyde of present embodiment, comprises the steps:

[0057] (a) Add 3 mol of 1,1,3,3-tetramethoxypropane to the reaction vessel at room temperature, add 0.2 mol of hydrochloric acid with a mass fraction of 8% under stirring conditions, control the reaction temperature at 25°C, and stir Reaction 3h.

[0058] (b) Add 1 mol of 1,4-dithio-2,5-diol and 0.7 mol of diethylamine to the mixture in the reaction vessel in step (a), control the reaction temperature to 70°C, and stir for 4 hours , to obtain 3-thiophene formaldehyde solution.

[0059] (c) Add the 3-thiophene formaldehyde solution obtained in step (b) dropwise to cold water at 10°C for quenching. After the dropwise addition, add toluene to the system for extraction and phase separation, and collect the organic phase; add to the organic phase wash with water, and then separate phases to collect the organic phase; concentrate the organic phase to remove excess raw materia...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a preparation method of 3-thiophenecarboxaldehyde. The preparation method of 3-thiophenecarboxaldehyde comprises thefollowing steps: performing reaction on 1,1,3,3-tetramethoxypropane under the acidic condition, performing mixed reaction on the reaction product and 1,4-dithio-2,5-diol under the alkaline conditionand performing aftertreatment to obtain the 3-thiophenecarboxaldehyde. By the preparation method of 3-thiophenecarboxaldehyde, the 3-thiophenecarboxaldehyde product with the purity exceeding 98 percent can be prepared only through simple mixing and stirring reaction, reaction does not need ultralow temperature and dangerous reagents in the preparation process, and the production safety coefficientis increased. Furthermore, the preparation method provided by the invention is simple in operation, the raw materials are easily available, operation cost and raw material cost are reduced, and the preparation method is suitable for industrialized 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 production capacity of thiophene formaldehyde in my country's enterprises is small, which restricts the development of this kind of medicine, and a new production method suitable for industrialization is urgently needed. [0003] In the prior art, there...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/22
CPCC07D333/22
Inventor 王武宝张雷孙方刚高小飞韩绍波
Owner 济南尚博医药股份有限公司
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