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Method for preparing 5,5-diphenyl-2-thiohydantoin

A technology of thiohydantoin and diphenyl, which is applied in the direction of organic chemistry, can solve problems such as difficulty in meeting environmental protection requirements, unsuitability for large-scale production, and high cost of raw materials, so as to reduce molar ratio, reduce production cost, and improve product yield. rate effect

Inactive Publication Date: 2012-10-10
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw material cost of the above-mentioned process is high, the amount of solvent is large, it is difficult to meet the environmental protection requirements, and it is not suitable for large-scale industrial production

Method used

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  • Method for preparing 5,5-diphenyl-2-thiohydantoin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 50mL of water to a 250mL Erlenmeyer flask with a condenser, then add benzil (50mmol), thiourea (80mmol) and sodium hydroxide (60mmol) together, reflux for 2h, stop heating, and continue stirring until the reaction Add 50mL of water when the liquid temperature is 50-60°C. Then slowly add hydrochloric acid with a mass concentration of 10% until the pH value of the solution is 6-7. Cool to room temperature, filter with suction, wash with water, and dry to obtain 13.4 g of a white crude product of 5,5-diphenyl-2-thiohydantoin with a yield of 100%. Recrystallization from ethanol gave 11.4 g of pure white product with a yield of 85% and a melting point of 234-237°C. As determined by liquid chromatography, the purity is 99.5%. The product has passed IR, 1 H NMR, 13 C NMR, mass spectrometry for characterization. The analysis results are as follows:

[0027] IR (KBr tablet method): 3260, 3161, 1748, 1725, 1598, 1584, 1531, 1496, 1447, 1382, 1168, 730, 694, 534cm -1 . ...

Embodiment 2

[0032] Add 30mL of water and 20mL of methanol into a 250mL Erlenmeyer flask with a condenser, then add benzil (50mmol), thiourea (80mmol) and potassium hydroxide (60mmol) together, reflux for 0.8h, stop heating, Continue to stir until the temperature of the reaction solution is 50-60°C, add 65mL of water. Then slowly add sulfuric acid with a mass concentration of 10% dropwise until the pH value of the solution is 4-5. Cool to room temperature, filter with suction, wash with water, and dry to obtain 13.4 g of a white crude product of 5,5-diphenyl-2-thiohydantoin with a yield of 100%. Recrystallization from ethanol gave 10.1 g of white pure product with a yield of 75% and a melting point of 232-236°C. As determined by liquid chromatography, the purity was 99.4%. The product has passed IR, 1 H NMR, 13 C NMR and mass spectrometry were used for characterization, and the characterization results were consistent with Example 1.

Embodiment 3

[0034] Add 35mL of water and 15mL of dimethyl sulfoxide into a 250mL Erlenmeyer flask with a condenser, then add benzil (50mmol), thiourea (100mmol), anhydrous potassium carbonate (15mmol) and sodium hydroxide (30mmol ) together, reflux for 3 hours, stop heating, and continue to stir until the temperature of the reaction solution is 50-60°C, add 70mL of water. Then slowly add hydrochloric acid with a mass concentration of 15% dropwise until the pH value of the solution is 5-6. Cool to room temperature, filter with suction, wash with water, and dry to obtain 10.6 g of a white crude product of 5,5-diphenyl-2-thiohydantoin with a yield of 79%. Recrystallization from ethanol gave 9.1 g of pure white product with a yield of 68% and a melting point of 233-237°C. As determined by liquid chromatography, the purity is 99.3%. The product has passed IR, 1 H NMR, 13 C NMR and mass spectrometry were used for characterization, and the characterization results were consistent with Exampl...

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Abstract

The invention belongs to the field of a preparation method for heterocyclic compounds, and in particular relates to a method for synthesizing 5,5-diphenyl-2-thiohydantoin by taking benzil and thiourea as original raw materials under an alkaline condition. The method comprises the following steps of: (1) adding the benzil, the thiourea, alkali and a solvent into a reaction kettle; (2) performing areflux reaction under a normal pressure condition; and (3) after the reaction ends, cooling, diluting, acidifying, separating and recrystallizing reaction liquid to obtain a target product, wherein in the step (1), the alkali is one or the mixture of hydroxide and carbonate; and the solvent is one or the mixture of more than two of water, dimethyl sulfoxide, acetone, tetrahydrofuran, acetonitrile, dioxane, methanol, ethanol and isopropanol. The invention has the advantages of readily available raw materials, temperate reaction condition, high yield, low cost and suitability for industrial mass production.

Description

technical field [0001] The invention belongs to the field of preparation methods of heterocyclic compounds, and in particular relates to a method for synthesizing 5,5-diphenyl-2-thiohydantoin under alkaline conditions using benzil and thiourea as starting materials. Background technique [0002] 2-Thiohydantoin derivatives have a wide range of biological activities, such as anticancer, antipathogen, antibacterial, antifungal, anticonvulsant, antispasmodic, antimutagenic and inducing lymphoproliferation. Moreover, it also has a good curative effect on the treatment of HSV, HIV and leukemia, and occupies an important position in organic synthesis. Among them, the more common 5,5-diphenyl-2-thiohydantoin (English name: 5,5-DIPHENYL-2-THIOHYDANTOIN) is a white crystal with a molecular formula of C 15 h 12 N 2 OS, melting point 234°C, molecular weight 268.33, structural formula: [0003] [0004] In the design of the 5,5-diphenyl-2-thiohydantoin synthesis process, ethanol ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/86
Inventor 王敏宋志国
Owner BOHAI UNIV
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