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Thiourea and oxazolidine thione compounds and synthesizing method and application thereof

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 high toxicity, low atomic economy, bad odor and the like

Active Publication Date: 2017-08-18
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 oxazolidine thione compounds and synthesizing method and application thereof
  • Thiourea and oxazolidine thione compounds and synthesizing method and application thereof
  • Thiourea and oxazolidine thione compounds and synthesizing method and application thereof

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preparation example Construction

[0058] The method for synthesizing thiourea and oxazolidinethione compounds of the present invention comprises the following steps: adding an amine compound (X mmol), a base (Y mmol), a solvent (V mL), and chloroform (Z mmol) in a reaction vessel, The reaction system was stirred at 55°C for 4 hours; after that, the reaction system was cooled to room temperature, amine compound (W mmol), sulfur powder (U mmol), and alkali (Hmmol) were added, and the reaction system was heated from room temperature to 55°C. conduct. Monitor the progress of the reaction. After the reaction was completed, at room temperature, saturated ammonium chloride solution (PmL) was added to the system to quench the reaction, extracted three times with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain target product.

[0059] The method for synthesizing thiourea and oxazolidinethione compounds of the present in...

Embodiment 1

[0061] Synthesis of compound 3k:

[0062]

[0063] In the reaction tube, add substrate 1k (0.2mmol, 45.8mg), potassium tert-butoxide (1.2mmol, 134.7mg), 1,4-dioxane / tert-butanol (0.4 / 0.4mL), chloroform in sequence (2 mmol, 238.8 mg), 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, the temperature was raised to 55° C. and the reaction was continued for 8 hours. Monitoring reaction process. After the reaction was completed, 3 mL of saturated ammonium chloride solution was added to the system to quench the reaction at room temperature, 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 the reaction tube, add substrate 1k (0.6mmol, 137.4mg), potassium tert-butoxide (1.2mmol, 134.7mg), 1,4-dioxane / tert-butanol (0.4 / 0.4mL), chloroform in sequence (2 mmol, 238.8 mg), 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, 3 mL of saturated ammonium chloride solution was added to the system to quench the reaction at room temperature, 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 process application, and in particular relates to thiourea and oxazolidinethione compounds and a synthesis method thereof, and their application in the fields of chiral thiourea catalyst, chiral oxazolidinethione prosthetic group, pesticide and pharmaceutical synthesis Applications. Background technique [0002] Thiourea and oxazolidinethione compounds are an important class of compounds, and many thiourea compounds exhibit excellent biological activities and are widely used in the fields of medicinal chemistry and pesticide chemistry. In addition, thiourea and oxazolidinethione compounds with chiral moieties can be used in the field of asymmetric synthesis as chiral thiourea catalysts and chiral chiral prosthetic groups. Therefore, it is particularly important to construct the C=S double bond from some raw materials with simple structure and commercial availability. [0003] [0004...

Claims

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Application Information

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Patent Type & Authority Applications(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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