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Preparation method of 2-sulfydryl-1-alkyl imidazole

A technology of alkylimidazole and mercapto, which is applied in the field of preparation of 2-mercapto-1-alkylimidazole, can solve problems such as potential safety hazards, spontaneous combustion and oxidation of sulfur powder, and non-parallel reaction yields, so as to avoid by-products, heavy Good performance, avoid spontaneous combustion and oxidation problems

Active Publication Date: 2017-12-29
浦拉司科技(上海)有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses more than 1 equivalent of sulfur powder. Excessive sulfur powder is easy to cause spontaneous combustion and oxidation, resulting in inconsistent reaction yields and potential safety hazards.

Method used

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  • Preparation method of 2-sulfydryl-1-alkyl imidazole
  • Preparation method of 2-sulfydryl-1-alkyl imidazole
  • Preparation method of 2-sulfydryl-1-alkyl imidazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of 2-mercapto-1-methylimidazole compound

[0024]

[0025] In the first step, take imidazole (34.0g, 0.5mol), sodium carbonate (106.0g, 1.0mol) and 800ml of acetone in a 1L autoclave, feed in methyl chloride (50.5g, 1.0mol), and stir vigorously at 60°C 12 hours, then down to room temperature, filter, wash the solid with 10% of the original volume of acetone, the organic phase is concentrated under reduced pressure to remove the solvent, and the remaining liquid is subjected to vacuum distillation (50 ~ 52 ° C, 1 torr), to obtain 36.5g of product N- Methylimidazole compound (2), yield 89%, purity 98.6%.

[0026] In the second step, add N-methylimidazole (36.5g, 0.45mol) and 220mL tetrahydrofuran obtained in the previous step into a three-necked reaction flask, then drop the temperature to -15°C and add 196mL (0.49mol) of n-butyllithium-n-hexane solution dropwise. , 2.5moL / L), after the dropwise addition, keep it at -15°C for 2 hours, then add elemental sulf...

Embodiment 2

[0029] Synthesis of 2-mercapto-1-methylimidazole compound

[0030]

[0031] In the first step, take imidazole (34.0g, 0.5mol), potassium carbonate (138.2g, 1.0mol) and 800ml of acetone in a 1L autoclave, feed methyl bromide (57.0g, 0.6mol), and stir vigorously at 60°C for 9 hours, then down to room temperature, filter, wash the solid with 10% of the original volume of acetone, the organic phase is concentrated under reduced pressure to remove the solvent, and the remaining liquid is subjected to vacuum distillation (50~52°C, 1torr), to obtain 37.4g of product N-formazan The imidazole compound (2) has a yield of 91% and a purity of 98.5%.

[0032] In the second step, add N-methylimidazole (37.4g, 0.46mol) and 220ml 2-methyltetrahydrofuran obtained in the previous step into a three-necked reaction flask, then cool down to -15°C and add n-butyllithium-n-hexane solution dropwise 191mL (0.48mol, 2.5moL / L), after the dropwise addition, keep the temperature at -15°C for 2 hours, ...

Embodiment 3

[0035] Synthesis of 2-mercapto-1-ethylimidazole compound

[0036]

[0037] In the first step, take imidazole (34.0g, 0.5mol), cesium carbonate (244.4g, 0.75mol) and 800ml acetone in a 1L autoclave, feed into ethyl chloride (48.4g, 0.75mol), and mechanically Stir for 12 hours, then cool down to room temperature, filter, wash the solid with 10% of the original volume of acetone, concentrate the organic phase under reduced pressure to remove the solvent, and carry out vacuum distillation (55~58°C, 1torr) for the remaining liquid to obtain 44.2g of product N - Ethyl imidazole compound (2), yield 92%, purity 98.8%.

[0038] In the second step, add N-ethylimidazole (44.2g, 0.46mol) obtained in the previous step and 250ml of diethoxymethane into a three-necked reaction flask, then cool down to -15°C and add n-butyllithium-n-hexane solution dropwise 193mL (0.48mol, 2.5moL / L), after the dropwise addition was completed, it was incubated and reacted at -15°C for 2 hours, and then ele...

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Abstract

The invention discloses a synthetic method of 2-sulfydryl-1-alkyl imidazole and belongs to the technical field of organic synthesis. The synthetic method comprises the following steps: in the presence of inorganic base, raising the temperature and then carrying out a sealing reaction on imidazole and alkyl halide to obtain 1-alkyl imidazole; dissolving 1-alkyl imidazole into an ether solvent, and adding 1 to 1.1 equivalent amount of butyl lithium at low temperature; then adding 0.9 to 0.95 equivalent amount of sulfur powder for carrying out a reflux reaction and adding acetylchloride after cooling to obtain 2-ethanethioate-1-alkyl imidazole; and finally, dissolving the 2-ethanethioate-1-alkyl imidazole into an alcohol solvent, adding hydrogen chloride or potassium carbonate with the catalytic amount for deprotection, thus obtaining the 2-sulfydryl-1-alkyl imidazole. The 2-sulfydryl-1-alkyl imidazole disclosed by the invention has the advantages of low price of raw materials and higher environmental-friendly property; in addition, the synthetic method is convenient to operate; and the quality of a product meets application standards of electronic chemicals.

Description

Technical field: [0001] The invention belongs to the field of organic chemistry, and in particular relates to a preparation method of 2-mercapto-1-alkylimidazoles. Background technique: [0002] Nitrogen heterocycles and their derivatives have a wide range of biological activities, and have extremely important application values ​​and occupy a very important position in various fields such as medicine, liquid crystal materials, and life sciences. Among nitrogen heterocycles, 2-mercapto-1-alkylimidazoles occupy a unique position in medicine and medicinal chemistry, and these compounds are also a common class of intermediates in synthetic chemistry. In recent years, due to the needs of new drug development, the synthesis methodology of mercaptoimidazole compounds or intermediates has received extensive attention. The synthetic method of the 2-mercapto-1-alkylimidazole of bibliographical information mainly contains two kinds: [0003] 1) Using halogenated acetaldehyde dimethy...

Claims

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Application Information

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IPC IPC(8): C07D233/84
CPCC07D233/84Y02P20/55
Inventor 漆伟君李静肖海旺
Owner 浦拉司科技(上海)有限责任公司
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