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Synthetic method of ammonium acetate-mediated benzothiazole compound

A synthetic method and benzothiazole technology, which is applied in the field of synthesis of benzothiazole compounds, can solve the problems of harsh reaction conditions and unstable reaction substrates, and achieve fewer reaction steps, high functional group tolerance, and mild reaction conditions Effect

Pending Publication Date: 2020-11-06
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction substrate is unstable, and the reaction conditions are relatively harsh

Method used

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  • Synthetic method of ammonium acetate-mediated benzothiazole compound
  • Synthetic method of ammonium acetate-mediated benzothiazole compound
  • Synthetic method of ammonium acetate-mediated benzothiazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]In a dry Schlenk reaction tube, add 2-iodo-4-methylaniline (0.2 mmol), potassium sulfide (0.6 mmol), dimethyl sulfoxide (2 mL), cuprous iodide (0.04 mmol), acetic acid Ammonium (1.2 mmol), water (80 ul), after adding the sample, vacuumize with an oil pump and inject nitrogen for gas replacement. After three replacements, stop the reaction at 140 °C for 10 hours, and cool to room temperature. The reaction was detected by thin-layer chromatography (TLC). After the reaction of the raw materials was completed, the reaction was terminated, and the mixed solution in the reaction tube was cooled to room temperature. Preliminary treatment of the mixture: pass through a short column, extract, collect the organic layer, spin the powder, and perform column chromatography to obtain the target product with a yield of 95%.

[0043] The hydrogen spectrogram and carbon spectrogram of gained target product are respectively as follows figure 1 and figure 2 As shown, the NMR data are a...

Embodiment 2

[0048] In a dry Schlenk reaction tube, add 2-iodo-4-methoxyaniline (0.2 mmol), potassium sulfide (0.6 mmol), dimethyl sulfoxide (2 mL), cuprous iodide (0.04 mmol), Ammonium acetate (1.2 mmol), water (80 ul), after adding the sample, vacuumize with an oil pump and inject nitrogen for gas replacement. After three replacements, stop the reaction at 140 °C for 11 hours, and cool to room temperature. The reaction was detected by thin-layer chromatography (TLC). After the reaction of the raw materials was completed, the reaction was terminated, and the mixed solution in the reaction tube was cooled to room temperature. Preliminary treatment of the mixture: pass through a short column, extract, collect the organic layer, spin the powder, and perform column chromatography to obtain the target product with a yield of 50%.

[0049] The hydrogen spectrogram and carbon spectrogram of gained target product are respectively as follows image 3 and Figure 4 As shown, the NMR data are as f...

Embodiment 3

[0054] In a dry Schlenk reaction tube, add 2-iodo-4-cyanoaniline (0.2 mmol), potassium sulfide (0.6 mmol), dimethyl sulfoxide (2 mL), cuprous iodide (0.04 mmol), acetic acid Ammonium (1.2 mmol), water (80 ul), after adding the sample, vacuumize with an oil pump and inject nitrogen for gas replacement. After three replacements, stop the reaction at 140 °C for 11 hours, and cool to room temperature. The reaction was detected by thin-layer chromatography (TLC). After the reaction of the raw materials was completed, the reaction was terminated, and the mixed solution in the reaction tube was cooled to room temperature. Preliminary treatment of the mixture: pass through a short column, extract, collect the organic layer, spin the powder, and perform column chromatography to obtain the target product with a yield of 95%.

[0055] The hydrogen spectrogram and carbon spectrogram of gained target product are respectively as follows Figure 5 and Figure 6 As shown, the NMR data are a...

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Abstract

The invention discloses a synthetic method of an ammonium acetate-mediated benzothiazole compound . The synthetic method comprises the steps: adding an o-haloaniline derivative, potassium sulfide, dimethyl sulfoxide, a catalyst, an additive 1 and an additive 2 into a reaction tube, carrying out a stirring reaction at the temperature of 130-150 DEG C, cooling to room temperature after the reactionis finished, and separating and purifying the product to obtain the benzothiazole compound. The invention provides the synthetic method of the benzothiazole compound by taking K2S as a sulfur source,DMSO as a carbon source and an oxidizing agent, an o-haloaniline derivative as a substrate and an ammonium acetate mediated three-component one-pot method. The method has the advantages of fewer reaction steps, mild reaction conditions, good functional group tolerance and the like.

Description

technical field [0001] The invention belongs to the field of benzothiazole compounds, and in particular relates to a synthesis method of benzothiazole compounds mediated by ammonium acetate. Background technique [0002] Benzothiazole is an important class of organic compounds. One is that benzothiazole is the core skeleton of benzothiazole derivatives, which has important application value in the fields of medicine and chemical industry; It is relatively active, and many methods for the synthesis of 2-substituted benzothiazole compounds have been developed by utilizing the C-H bond functionalization at the 2nd position (A. Arora, J. D. Weaver, Org. Lett . 2016, 18 , 3996; X. Dai, Y. Zhu, Z. Wang, J. Weng, Chin. J. Org. Chem. 2017, 37, 1924.), is an important raw material for the synthesis of 2-substituted benzothiazole compounds. However, compared with the report on the synthesis method of 2-substituted benzothiazole compounds, the research report on the synthesis m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/62C07D277/84C07D513/04
CPCC07D277/62C07D277/84C07D513/04
Inventor 朱小明王志强王成勇张复兴邝代治
Owner HENGYANG NORMAL UNIV
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