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Synthesis method of benzothiophene compound

A benzothiophene and synthesis method technology, applied in the field of organic compounds and synthesis, can solve the problems of large substrate limitations, increased production costs, and large environmental pollution, and achieve simple processing, high use safety, and low environmental pollution. Effect

Inactive Publication Date: 2017-10-03
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the above synthesis methods of benzothiophene compounds, the substrates of some reactions are limited, and many of them need to be pre-synthesized. Some methods use chemical oxidants and metal catalysts, which increase the production cost and cause great environmental pollution.
Some methods produce halogen-containing by-products, which limit their application

Method used

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  • Synthesis method of benzothiophene compound
  • Synthesis method of benzothiophene compound
  • Synthesis method of benzothiophene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Synthesis of dimethyl 5-methylbenzothiophene-2,3-dicarboxylate (compound A)

[0024] Magnets were added to a 25ml round bottom flask, followed by the compound p-Cresol (0.5mmol) and compound Dimethyl butynedioate (1mmol), 1,2-dioxane (10ml) were added to a round bottom flask at 80 o Stir at C for 4h, remove the solvent by distillation under reduced pressure, and carry out column chromatography separation (silica gel: 200~300 mesh, the eluent is a volume ratio of petroleum ether:ethyl acetate=50:1v / v), and remove the solvent by distillation under reduced pressure. solvent to obtain a white powdery pure product, dimethyl 5-methylbenzothiophene-2,3-dicarboxylate (Compound A), with a yield of 90%. Its synthetic formula is as follows:

[0025]

[0026] The NMR data of Compound A are as follows: 1 H NMR (600 MHz, CDCl 3 ) δ 7.72 (d, J = 8.4 Hz, 1H), 7.70 (s, 1H), 7.31 (d, J = 8.3 Hz, 1H), 4.02 (s, 3H), 3.93 (s, 3H). 13 C NMR (151 MHz, CDCl 3 ) δ 1...

Embodiment 2

[0027] Example 2: Synthesis of Dimethyl Benzothiophene-2,3-dicarboxylate (Compound B)

[0028] Magnets were added to a 25ml round bottom flask, followed by the compound Thiophenol (0.5mmol) and compound Dimethyl butynedioate (1mmol), 1,2-dioxane (10ml) were added to a round bottom flask at 80 o Stir for 2 hours at C, remove the solvent by distillation under reduced pressure, and carry out column chromatography separation (silica gel: 200~300 mesh, the eluent is a volume ratio of petroleum ether:ethyl acetate=50:1v / v), and remove the solvent by distillation under reduced pressure. solvent, the pure product was obtained as white powder, namely dimethyl benzothiophene-2,3-dicarboxylate (compound B), and the yield was 70%. Its synthetic formula is as follows:

[0029]

[0030] The NMR data of Compound B are as follows: 1 H NMR (600 MHz, CDCl 3 ) δ 7.93 (d, J= 7.7 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.50 - 7.43 (m, 2H), 4.02 (s, 3H), 3.94 (s, 3H). 13 CNMR (151 MHz, CDC...

Embodiment 3

[0031] Example 3: Synthesis of dimethyl 7-methylbenzothiophene-2,3-dicarboxylate (compound C)

[0032] Compound Ⅰ is o-methylthiophenol (0.5mol), compound It is dimethyl butynedioate (1mol), and the reaction time is 2h; the synthesis route and separation method are basically the same as in Example 1. The white powdery product obtained was dimethyl 7-methylbenzothiophene-2,3-dicarboxylate (compound C), and the yield was 85%. Its synthetic formula is as follows:

[0033]

[0034] The NMR data of Compound C are as follows: 1 H NMR (600 MHz, CDCl 3 ) δ 7.76 (d, J = 8.2 Hz, 1H), 7.38 (t, J = 7.7 Hz, 1H), 7.28 (d, J = 7.2 Hz, 1H), 4.02 (s, 3H), 3.95 (s,3H), 2.56 (s, 3H). 13 C NMR (151 MHz, CDCl 3 ) δ 165.0, 162.2, 140.7, 136.6, 134.0, 132.4, 132.2, 127.5, 126.1, 122.1, 52.9, 52.8, 20.0.

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Abstract

The invention provides a synthesis method of a benzothiophene compound. The synthesis method comprises the steps of allowing thiophenol and a derivative to react with butyne dicarboxylic acid diester at a mole ratio of 1:1-1:3 in an organic solvent under an air or oxygen atmosphere for 2-8h at 20-90 DEG C, performing reduced pressure distillation to remove the solvent, then performing column chromatography separation, and obtaining the target compound. A reaction reagent is low in price; a reaction step is short; a reaction condition is mild; a yield is high; the purity is good; the post-treatment is simple; the industrial production cost can be effectively lowered; the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing benzothiophene compounds, belonging to the technical field of organic compounds and synthesis. Background technique [0002] Benzothiophenes are an important class of heterocyclic compounds, which are widely used in medicine, dyes, materials and other fields. Many drug molecules contain benzothiophene structure, such as Raloxifene (Raloxifene) is a non-hormonal drug, which has estrogen stimulant effect on bone and cardiovascular system, estrogen antagonism effect on breast and uterus, has Mimic estrogen effect, but without many adverse effects of estrogen. Zileuton (Zileuton) is an orally active inhibitor of 5-lipoxygenase, which is mainly used for the prevention and maintenance treatment of chronic asthma patients over 12 years old. Benzothiophene fused ring compounds can be used as field-effect transistors, light-emitting diodes, and photovoltaic cells. [0003] At present, the main methods for sy...

Claims

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Application Information

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IPC IPC(8): C07D333/70C07D333/74
CPCC07D333/70C07D333/74
Inventor 霍聪德王亚军
Owner NORTHWEST NORMAL UNIVERSITY
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