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Method for preparing tetrahydrothiazole diketone derivatives

A technology for thiazolidinedione and derivatives, which is applied in the field of preparation of thiazolidinedione derivatives, can solve problems such as high reaction temperature, low production efficiency, and environmental pollution, and achieve simple process operation, reduced production cost, and product separation simple effect

Inactive Publication Date: 2008-10-29
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Usually, the synthetic method of this class compound is in organic acid, alkali or salt (as: piperidine, morphine, acetic acid sodium, potassium acetate, ammonium acetate, piperidine-acetic acid) catalyzed to complete, these methods or because of high reaction temperature, long time, there is the problem of low production efficiency, or because of the use of volatile, environmentally unfriendly solvents, resulting in Pollution of the environment, these affect the social effects of the application of the drug

Method used

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  • Method for preparing tetrahydrothiazole diketone derivatives
  • Method for preparing tetrahydrothiazole diketone derivatives
  • Method for preparing tetrahydrothiazole diketone derivatives

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preparation example Construction

[0025] Preparation of [Bmim]OH Ionic Liquid

[0026] 1. Preparation of [Bmim]Br

[0027] Heat 0.5mol N-methylimidazole to 70°C in advance, and slowly add 0.55mol bromobutane dropwise under strong stirring. After the dropwise addition, continue to raise the temperature to 90°C, and keep the reaction for 5h.

[0028] To the end of the reaction, the reaction solution was poured out, washed with ethyl acetate for 3 to 4 times, and the washed reaction solution was rotary evaporated to remove residual ethyl acetate to obtain a white solid [Bmim]Br.

[0029] 2. Preparation of [Bmim]OH from [Bmim]Br

[0030] Take 0.3mol [Bmim]Br and 0.3mol potassium hydroxide, add 100ml of anhydrous dichloromethane as solvent, stir at room temperature for 10h, and end the reaction. The precipitate was removed by filtration, the filtrate was rotary evaporated to remove dichloromethane, and then washed with diethyl ether for 3 to 4 times to obtain the basic ionic liquid [Bmim]OH.

Embodiment 1

[0032] Preparation of 5-(4-dimethylamino)-benzylidene-2,4-thiazolidinedione

[0033]

[0034] Add 4mmol of 2,4-thiazolidinedione and 4mmol of p-dimethylaminobenzaldehyde into a 25ml round bottom flask, add 20ml of ionic liquid [Bmim]OH, stir at 100°C, and track the reaction process by thin layer chromatography (TLC). After about 10 hours, the reaction was completed. Add 2ml of distilled water to the reaction solution, continue to stir, stop stirring after 5min, filter, wash the residue once with distilled water, and collect the crude product after drying. The crude product was recrystallized with absolute ethanol to obtain the pure product 5-(4-dimethylamino)benzylidene-2,4-thiazolidinedione compound with a yield of 92%, m.p: 296-297°C, purity 99%.

[0035] Recovery of ionic liquid: Distill the filtered filtrate at 75-80°C to remove moisture under reduced pressure to obtain pure ionic liquid for the next round of preparation.

[0036] Characterization of this compound: 1...

Embodiment 2

[0038] Preparation of 5-(4-methoxy)-benzylidene-2,4-thiazolidinedione

[0039]

[0040] Add 0.8mmol of 2,4-thiazolidinedione and 4mmol of p-methoxybenzaldehyde into a 25ml round bottom flask, add 8ml of ionic liquid [Bmim]OH, stir at 100°C, and track the reaction process by thin layer chromatography (TLC) After about 10 hours, the reaction was completed. Add 2ml of distilled water to the reaction solution, continue to stir, stop stirring after 5min, filter, wash the residue once with distilled water, and collect the crude product after drying. The crude product was recrystallized with absolute ethanol to obtain the pure product 5-(4-methoxy)benzylidene-2,4-thiazolidinedione compound with a yield of 91%, m.p: 218-219°C, purity 99%.

[0041] Recovery of ionic liquid: Distill the filtered filtrate at 75-80°C to remove moisture under reduced pressure to obtain pure ionic liquid for the next round of preparation.

[0042] Characterization of this compound: 1 H NMR (400MHz, DM...

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Abstract

The invention discloses a method for preparing thiazolidinedione derivatives using an aromatic aldehyde and 2,4-thiazolidinedione as raw materials, ionic liquid [Bmim]OH as catalyst and solvent. The preparation method has the advantages of simple process operation, short reaction time, no pollution, and fulfillment of green chemistry requirements. The obtained product can be simply separated, and has yield of 85-92% and purity up to over 98%.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, and in particular relates to a method for preparing thiazolidinedione derivatives. Background technique [0002] In recent years, with the development of social economy and the improvement of residents' living standards in various countries in the world, the incidence and prevalence of diabetes have increased year by year, the reduction of physical activity, changes in dietary structure and other unhealthy lifestyles and global aging results have further promoted II prevalence of type 2 diabetes. Therefore, diabetes has become a major social problem threatening people's health. [0003] Diabetes is a lifelong disease with many types of complications and great harm, seriously affecting the quality of life of patients. At the same time, the high prevalence of the disease has brought a heavy burden to patients, families and society. 95% of diabetes is type II diabetes, the main cause of the disea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/34C07D417/06B01J31/02
Inventor 胡燚黄和谢涛余定华胡耀池曾必文
Owner NANJING UNIV OF TECH
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