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Process for synthesizing thiolactone

A synthesis process, thiolation technology, applied in the direction of organic chemistry, can solve the problems of high unit consumption, large environmental pollution, low yield, etc., and achieve the effect of increasing reaction yield, reducing cost, and easily obtaining raw materials

Inactive Publication Date: 2008-01-02
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, sulfur-containing reagents such as thioacetamide or potassium thioacetate and thiocyanate all have poor stability, large environmental pollution, high unit consumption, incomplete thiolation, and low yield (generally at 70-80%). Problems such as high cost (Shimaji K, Aoki Y., Maejima K., et al., JP54112886; Aoki Y., Suzuki H., Akigama H., et al., DE 605968); especially high temperature and high humidity in summer It is very easy to deteriorate, resulting in a decrease in sulfur content, which in turn reduces the yield and increases impurities, and is not suitable for industrial production
If one tries to carry out this reaction directly with common thiolation reagents such as phosphorus pentasulfide, the reaction cannot be carried out due to the low reactivity of the lactone

Method used

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  • Process for synthesizing thiolactone
  • Process for synthesizing thiolactone
  • Process for synthesizing thiolactone

Examples

Experimental program
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Effect test

Embodiment 1

[0026] In a 500ml three-necked flask with a reflux condenser, a stirrer, and a thermometer, add 20.0g (0.062mol) of raw material lactone, 10g (0.045mol) of phosphorus pentasulfide, 2.6g (0.044mol) of acetamide, N,N-dimethyl 150ml of formamide solution was heated in an oil bath to control the external temperature to 150°C, kept at reflux for 2 hours, and the reaction was complete by HPLC detection. Control the external temperature below 100°C, recover N,N-dimethylformamide under reduced pressure to obtain a dark brown solid, add 200ml of toluene while it is hot, stir to form a uniform suspension, add 5% hydrochloric acid dropwise, and adjust the pH to PH =2, separate the organic layer, then extract the aqueous layer with 50ml of toluene, combine the organic layers, wash the organic layer with saturated aqueous sodium bicarbonate solution to neutrality, then wash it once with deionized water, recover the toluene under reduced pressure to obtain a slightly pink color Solid, soake...

Embodiment 2

[0033] In a 500ml three-neck flask equipped with a co-current condenser, a stirrer, and a thermometer, add 20.0g (0.062mol) of raw material lactone, 10g (0.045mol) of phosphorus pentasulfide, 0.3g (0.005mol) of acetamide, N,N-dimethyl 150ml of methyl formamide solution, heated in an oil bath to control the external temperature of 150°C, and kept at reflux for 2 hours. The HPLC detection reaction was carried out by about 70%, and the HPLC detection reaction was basically complete after continuing to react for 3 hours. The aftertreatment method is the same as in Example 1 to obtain a white solid, which is 19.5g after vacuum drying, with a melting point of 125-127°C and an optical rotation [α] D 25 =+91.8 0 (c1.0, CHCl 3 ), the HPLC content is 98.7%, and the yield is 93.2%.

Embodiment 3

[0035] Others are the same as in Example 2, the amount of acetamide charged is 3 g (0.05 mol), and the reflux reaction is carried out for 1.5 h to obtain 19.0 g of the product with a yield of 90.4%.

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Abstract

The invention discloses a synthesizing method of (3aS, 6aR)-1, 3-dibenzyl-6H-1H-thiofuran [3, 4-d] imidazole-2, 4-diketone, which is reacted by (3aS, 6aR)-1, 3-dibenzyl-6H-1H-furan [3, 4-d] imidazole-2, 4-diketone in the active thio agent system with phosphorus pentasulfide and acetamide. The invention can recycle the reacting product to save cost greatly, which improves the receiving rate.

Description

technical field [0001] The present invention relates to the key intermediate of vitamin H, thiolactone (3aS, 6aR)-1,3-dibenzyl-hexahydro-1H-thieno[3,4-d]imidazole-2,4-di The invention relates to a synthesis technique of ketone, which belongs to the technical field of chemical synthesis. Background technique [0002] D-biotin (d-Biotin), also known as vitamin H or coenzyme R, chemical name (3aS, 4S, 6aR)-hexahydro-2-oxo-thieno[3,4-d]imidazole-4-pentanoic acid , belonging to the water-soluble B vitamins, is necessary for the entire biological world. Biotin plays an important role in maintaining normal animal development, reproduction and maintaining healthy skin, feathers and bones. At present, Xinchang Pharmaceutical Factory of Zhejiang Pharmaceutical Co., Ltd. is the largest D-biotin producer in the world, and its output accounts for more than 50% of the world's total. [0003] [0004] Vitamin H [0005] (3aS, 6aR)-1,3-dibenzyl-hexahydro-1H-thieno[3,4-d]imidazole-2,4...

Claims

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Application Information

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IPC IPC(8): C07D495/04
Inventor 沈润溥刘伟傅建中蒋定强黄忠印
Owner SHAOXING UNIVERSITY
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