Method for synthesizing 2-substituted benzothiazole by one-pot method

A technology for benzothiazoles and compounds, which is applied in the field of one-pot synthesis of 2-substituted benzothiazoles, can solve the problems of restricted reaction conditions in the reaction process, expensive catalysts, complex reaction conditions, etc., and achieve the conversion rate of the substrate and the product The effect of high yield, expanding industrial application, and high reaction yield

Active Publication Date: 2020-02-28
NANJING UNIV OF TECH
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  • Claims
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Problems solved by technology

(Y L LAI, J S YE, J MHUANG.ChemEur J, 2016, 22(15): 5425~5429.) However, these synthetic methods use more expensive catalysts and the reaction conditions are more complicated
[0004] However, there are some defects in the above-mentioned various methods, such as expensive substrate raw materials, complicated reaction steps, harsh conditions, complicated post-treatment, high price, complicated reaction process and harsh reaction conditions. Its industrial application in many fields

Method used

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  • Method for synthesizing 2-substituted benzothiazole by one-pot method
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  • Method for synthesizing 2-substituted benzothiazole by one-pot method

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Embodiment 1

[0026] This embodiment is the synthesis of 2-benzylbenzothiazole, with o-iodoaniline, styrene, sulfur powder, K 2 HPO 4 , CuCl 2 2H 2 O, 1,10-phen, N,N-dimethylformamide are used as raw materials, and the reaction formula is as follows:

[0027]

[0028] Preparation method: add 0.5mmol o-iodoaniline, 1.0mmol styrene, 1.50mmol sulfur powder, 1.50mmol K 2 HPO 4 , 0.1mmol CuCl 2 2H 2 O, 0.1 mmol 1,10-phen, and 2.5 mL N,N-dimethylformamide were added, and stirred at 130°C for 12 hours under a nitrogen atmosphere. After the reaction was completed, the TLC plate detected that a product was formed.

[0029] The reaction solution was cooled, extracted, dried, distilled under reduced pressure, column chromatography and filtered to obtain a brown oil.

[0030] Yield 78%, this 2-benzylbenzothiazole H NMR 1 H NMR (300MHz, Chloroform-d) δ8.01(d, J=8.1Hz, 1H), 7.79(d, J=7.9Hz, 1H), 7.46(t, J=7.7Hz, 1H), 7.36(dd ,J=7.3,3.7Hz,6H),4.45(s,2H).

Embodiment 1-1

[0032] This embodiment is the synthesis of 2-benzylbenzothiazole, with o-iodoaniline, styrene, sulfur powder, K 2 HPO 4 , CuCl 2 2H 2 O, 1,10-phen, N,N-dimethylformamide are used as raw materials, and the reaction formula is as follows:

[0033]

[0034] Preparation method: Add 0.5mmol o-iodoaniline, 0.5mmol styrene, 1.50mmol sulfur powder, 1.50mmol K 2 HPO 4 , 0.1mmol CuCl 2 2H 2 O, 0.1 mmol 1,10-phen, and 2.5 mL N,N-dimethylformamide were added, and stirred at 130°C for 12 hours under a nitrogen atmosphere. After the reaction was completed, the TLC plate detected that a product was formed.

[0035] The reaction solution was cooled, extracted, dried, distilled under reduced pressure, column chromatography and filtered to obtain a brown oil.

[0036] Yield 55%, this 2-benzylbenzothiazole NMR 1H NMR (300MHz, Chloroform-d) δ8.01(d, J=8.1Hz, 1H), 7.79(d, J=7.9Hz, 1H), 7.46(t, J=7.7Hz, 1H), 7.36(dd ,J=7.3,3.7Hz,6H),4.45(s,2H).

Embodiment 1-2

[0038] This embodiment is the synthesis of 2-benzylbenzothiazole, with o-iodoaniline, styrene, sulfur powder, K 2 HPO 4 , CuCl 2 2H 2 O, 1,10-phen, N,N-dimethylformamide are used as raw materials, and the reaction formula is as follows:

[0039]

[0040] Preparation method: Add 0.5mmol o-iodoaniline, 1.5mmol styrene, 1.50mmol sulfur powder, 1.50mmol K 2 HPO 4 , 0.1mmol CuCl 2 2H 2 O, 0.1 mmol 1,10-phen, and 2.5 mL N,N-dimethylformamide were added, and stirred at 130°C for 12 hours under a nitrogen atmosphere. After the reaction was completed, the TLC plate detected that a product was formed.

[0041] The reaction solution was cooled, extracted, dried, distilled under reduced pressure, column chromatography and filtered to obtain a brown oil.

[0042] Yield 59%, this 2-benzylbenzothiazole H NMR 1 H NMR (300MHz, Chloroform-d) δ8.01(d, J=8.1Hz, 1H), 7.79(d, J=7.9Hz, 1H), 7.46(t, J=7.7Hz, 1H), 7.36(dd ,J=7.3,3.7Hz,6H),4.45(s,2H).

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Abstract

The invention relates to a method for synthesizing 2-substituted benzothiazole by a one-pot method. The preparation method comprises the following specific steps: dissolving a 2-Iodoaniline compound,a styrene compound, elemental sulfur, an alkaline medium, a catalyst and a ligand in an organic solvent, and stirring for 10-24 hours at 100-140 DEG C to react to obtain 2-substituted benzothiazole; wherein the molar ratio of the 2-Iodoaniline compound to the styrene compound is 1: (1-3); and cooling, extracting, drying and column chromatography separation are carried out to obtain a pure product.The method has the advantages that (1) the reaction conditions are mild, the reaction activity is high, the reaction yield is high, the product selectivity is high, and the substrate expansion rangeis wide; (2) use of a large amount of solvents and noble metal compounds in a catalyst system is avoided, cost is low, the method is safe and convenient, and low environmental pollution is caused by the reaction system; and (3) no mixed solvent or oxygen is used in the reaction system, so that potential risks existing in oxygen use are avoided, and a reference value is provided for industrial application.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 2-substituted benzothiazoles in one pot. Background technique [0002] Benzothiazole heterocycles are a unique and multifunctional important ligand in drug molecule design and medicinal chemistry. It has a broad spectrum of biological activities and is widely used as an intermediate in organic synthesis in agriculture, medicine and industry. field. It has played important pharmacological activities in anti-tumor, anti-tuberculosis, anti-convulsion, antimalarial, hypoglycemic, antibacterial, anthelmintic, analgesic, anti-inflammatory and diuretic. At the same time, some benzothiazole derivatives are used as vulcanization accelerators It is also a synthetic raw material for drugs and plays an important role in the bioactivity of amyloid imaging. With the continuous progress and development of science and technology, the application of benzothiazole compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/64
CPCC07D277/64
Inventor 韩世清张俊刘雅菲张育榕呼亮
Owner NANJING UNIV OF TECH
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