Thiourea and oxazolidinethione compounds and their synthesis method and application

A technology of oxazolidinethione and synthesis method, applied in organic chemistry methods, chemical instruments and methods, organic chemistry and other directions, can solve the problems of low atom economy, high toxicity, bad odor and the like

Active Publication Date: 2019-05-17
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The traditional method of synthesizing thiourea and oxazolidinethiones is mainly by using carbon disulfide, thiophosgene, Lawson's reagent, phosphorus pentasulfide or their derivatives as thiocarbonylation reagents, but these reagents are often flammable and highly A series of problems such as toxicity, low atom economy, and bad smell

Method used

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  • Thiourea and oxazolidinethione compounds and their synthesis method and application
  • Thiourea and oxazolidinethione compounds and their synthesis method and application
  • Thiourea and oxazolidinethione compounds and their synthesis method and application

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[0058] The synthetic method of thiourea and oxazolidinethione compound of the present invention comprises the following steps: in reaction vessel, add amine compound (X mmol), alkali (Ymmol), solvent (V mL), chloroform (Z mmol), The reaction system was stirred at 55°C for 4 hours; afterward, the reaction system was cooled to room temperature, and an amine compound (W mmol), sulfur powder (U mmol), and alkali (Hmmol) were added, and the reaction system was heated at room temperature to 55°C. conduct. Monitor the progress of the reaction. After completion of the reaction, at room temperature, add saturated ammonium chloride solution (PmL) to the system to quench the reaction, extract 3 times with ethyl acetate, dry the organic phase with anhydrous sodium sulfate, filter, concentrate, and separate by column chromatography to obtain target product.

[0059] The synthetic method of thiourea and oxazolidinethione compound of the present invention comprises the following steps: in ...

Embodiment 1

[0061] Synthesis of compound 3k:

[0062]

[0063] In a reaction tube, sequentially add substrate 1k (0.2mmol, 45.8mg), potassium tert-butoxide (1.2mmol, 134.7mg), 1,4-dioxane / tert-butanol (0.4 / 0.4mL), chloroform (2mmol, 238.8mg), the reaction system was stirred at 55°C for 2 hours. Then, the reaction was cooled to room temperature, and sulfur powder (0.6mmol, 19.2mg), potassium tert-butoxide (0.4mmol, 44.9mg), 2k (0.24mmol, 29.0mg) were added successively, and the temperature was raised to 55°C to continue the reaction for 8 hours, monitoring reaction process. After the reaction was completed, at room temperature, 3 mL of saturated ammonium chloride solution was added to the system to quench the reaction, extracted three times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain the compound 3k (36.8 mg, 47%).

Embodiment 2

[0065] Synthesis of compound 3k:

[0066]

[0067]In a reaction tube, sequentially add substrate 1k (0.6mmol, 137.4mg), potassium tert-butoxide (1.2mmol, 134.7mg), 1,4-dioxane / tert-butanol (0.4 / 0.4mL), chloroform (2mmol, 238.8mg), the reaction system was stirred at 55°C for 2 hours. Then, the reaction was cooled to room temperature, and sulfur powder (0.6mmol, 19.2mg), potassium tert-butoxide (0.4mmol, 44.9mg), 2k (0.2mmol, 24.2mg) were added successively, and the temperature was raised to 55°C to continue the reaction for 8 hours, monitoring reaction process. After the reaction was completed, at room temperature, 3 mL of saturated ammonium chloride solution was added to the system to quench the reaction, extracted three times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain the compound 3k (55.7 mg, 71%).

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Abstract

The invention discloses thiourea and oxazolidine thione compounds shown in formulas (3) and (5) and a synthesizing method and application thereof. The synthesizing method comprises the following steps of in a reaction solvent, using primary amine, secondary amine and other amine compounds as raw materials, using an inorganic vulcanizing reagent as a sulfur source, using single-carbon halohydrocarbon as a single-carbon source, and under the action of alkaline, reacting to obtain the thiourea and oxazolidine thione compounds shown in the formulas (3) and (5). The synthesizing method has the advantages that the cost of the raw materials is low, the obtaining is easy, the reaction is simple, and the tolerability of functional groups is strong; the use of main thiocarbonyl reagents, such as volatile and flammable carbon disulfide, high-toxic and strong-corrosive thiophosgene, and high-toxic and smelly-odor Lawesson reagent or phosphorus pentasulfide, is avoided; the synthesizing method is successfully applied to the gram-level synthesizing of chiral thiourea catalysts, chiral oxazolidine thione prothetic groups and commercial pesticide; the practical value is stronger, and the application prospect is wide.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to thiourea and oxazolidinethione compounds and their synthesis methods and their applications in the fields of chiral thiourea catalysts, chiral oxazolidinethione prosthetic groups, pesticides and drug synthesis Applications. Background technique [0002] Thiourea and oxazolidinethiones are an important class of compounds. Many thiourea compounds exhibit excellent biological activities and are widely used in the fields of medicinal chemistry and agrochemical chemistry. In addition, thiourea and oxazolidinethione compounds with chiral segments can be used as chiral thiourea catalysts and chiral prosthetic groups in the field of asymmetric synthesis. Therefore, it is particularly important to construct C=S double bonds from some simple and commercially available raw materials. [0003] [0004] Representative important thioureas and oxa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C335/16C07C335/18C07C335/12C07C335/14C07D295/215C07D295/135C07D209/14C07F17/02C07D471/08C07D263/16C07D263/62C07D263/58C07D413/06C07D233/42C07D235/28C07D239/10C07D239/78
CPCC07B2200/07C07C335/12C07C335/14C07C335/16C07C335/18C07D209/14C07D233/42C07D235/28C07D239/10C07D239/78C07D263/16C07D263/58C07D263/62C07D295/135C07D295/215C07D413/06C07D471/08C07F17/02
Inventor 姜雪峰谭伟
Owner EAST CHINA NORMAL UNIV
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