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The method for preparing thioamide compound

A thioamide and compound technology, which is applied in the field of organic synthesis, can solve the problems of unstable Lawson reagent or thiophosphine reagent, harsh reaction conditions of substrates, and poor universality of substrates, so as to improve atom economy, The effect of protecting the health of environmental operators and ensuring the health of operators

Active Publication Date: 2022-05-13
QUZHOU RES INST OF ZHEJIANG UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The earliest method for synthesizing thioamides is to carry out the sulfidation of carbonamide by amide and Lawson's reagent or phosphorus pentasulfide (Chem.Commun.2009,46,7122.); Reagents are unstable, expensive, low atom economy, smelly, unfriendly to the environment, etc.
Although this method improves the atomic utilization rate and step economy of the reaction, the substrates are not universally applicable, and the reaction conditions of some substrates are harsh, and the reaction temperature can reach up to 320 °C. limits its usefulness

Method used

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  • The method for preparing thioamide compound
  • The method for preparing thioamide compound

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Experimental program
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Effect test

Embodiment 1

[0037] Embodiment 1, a kind of preparation method of thioamide compound, take benzyl formate as raw material:

[0038] Under nitrogen protection, benzyl formate (0.53g, 3.9mmol), sublimed sulfur (0.25g, 7.8mmol), and cesium carbonate (0.32g, 1.0mmol) were added to 2.7mL formamide, and at a reaction temperature of 80°C, The reaction was stirred for 4 hours.

[0039] After the reaction was completed, 2.7 mL of deionized water was added to the resulting reaction liquid to quench the reaction liquid, followed by extraction with ethyl acetate (2.7 mL×3) to obtain an aqueous phase and an organic phase, respectively, and then saturated saline (2.7 mL ×3) Wash the organic phase, and dry it with anhydrous sodium sulfate, filter (remove sodium sulfate), concentrate by rotary evaporation (remove ethyl acetate), purify by silica gel (100-200 mesh) column chromatography, and use ethyl acetate / petroleum The mixed solution of ether (1:12 volume ratio) is used as eluent, and the consumption ...

Embodiment 2

[0040] Embodiment 2, a kind of preparation method of thioamide compound, benzyl formate is raw material:

[0041] Under nitrogen protection, benzyl formate (0.53g, 3.9mmol), sublimed sulfur (0.25g, 7.8mmol), and cesium carbonate (0.44g, 1.4mmol) were added to 4.2mL N,N-dimethylformamide, At a reaction temperature of 60°C, the reaction was stirred for 8 hours.

[0042] After the reaction was completed, 4.2 mL of deionized water was added to the resulting reaction liquid to quench the reaction liquid, followed by extraction with ethyl acetate (4.2 mL × 3) to obtain an aqueous phase and an organic phase, respectively, and then saturated brine (4.2 mL ×3) The organic phase was washed, dried with anhydrous sodium sulfate, filtered, concentrated by rotary evaporation, purified by silica gel (100-200 mesh) column chromatography, and purified with a mixture of ethyl acetate / petroleum ether (1:15 volume ratio) As the eluent, the amount of the eluent is 350ml, all the eluate is collect...

Embodiment 3

[0043] Embodiment 3, a kind of preparation method of thioamide compound, take benzyl acetate as raw material:

[0044] Under nitrogen protection, benzyl acetate (0.59g, 3.9mmol), sublimed sulfur (0.20g, 6.2mmol), cesium hydroxide (0.26g, 1.8mmol) were added to 4.1mL N-methylformamide, at 70 °C reaction temperature, the reaction was stirred for 7 hours.

[0045] After the reaction was completed, 4.1 mL of deionized water was added to the resulting reaction liquid to quench the reaction liquid, followed by extraction with ethyl acetate (4.1 mL×3) to obtain an aqueous phase and an organic phase, respectively, and then saturated brine (4.1 mL ×3) The organic phase was washed, dried with anhydrous sodium sulfate, filtered, concentrated by rotary evaporation, purified by silica gel (100-200 mesh) column chromatography, and purified with a mixture of ethyl acetate / petroleum ether (1:15 volume ratio) As an eluent, the amount of eluent is 350ml, all the eluents are collected, and conc...

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Abstract

The invention discloses a method for preparing thioamide compounds: under the protection of an inert gas, a carboxylate is used as a substrate, sublimed sulfur is used as a sulfur source, an alkali is used as a catalyst, and formamide is used as a solvent and an amine source. Under the reaction temperature of ℃, stirring and reacting for 4 to 8 hours; post-processing the reaction product to obtain thioamide compounds. The present invention synthesizes thioamide compounds through a three-component one-pot method of carboxylate, sublimated sulfur, and formamide; the method has the advantages of mild and safe operating conditions, short reaction time, simple process, easy operation, and no need for special instruments , high product yield and other technical advantages.

Description

technical field [0001] The invention relates to a method for synthesizing a class of organic compounds, in particular to the synthesis of a class of pharmaceutical intermediates containing thioamide structural units, and belongs to the field of organic synthesis. Background technique [0002] Thioamide structure, as an important structural unit in C=S double bond compounds, is widely present in drug molecules and has strong pharmaceutical activity; meanwhile, it is also used to construct various sulfur-containing heterocycles (such as thiazole, thiazoline, thiazole Ketones, etc.) one of the most important precursors (Org. Lett. 2016, 18, 356.). [0003] The earliest method for synthesizing thioamides is to carry out the sulfidation of carbonamide by amide and Lawson's reagent or phosphorus pentasulfide (Chem.Commun.2009,46,7122.); Reagents are unstable, expensive, low atom economy, smelly, unfriendly to the environment, etc. [0004] In recent years, the use of Willgerodt-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C327/44C07D295/194C07D213/83C07D333/38C07D307/68C07C327/42C07D307/16
CPCC07C327/44C07D295/194C07D213/83C07D333/38C07D307/68C07C327/42C07D307/16C07C2601/14
Inventor 钱超靳浩阮建成周少东陈新志
Owner QUZHOU RES INST OF ZHEJIANG UNIV
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