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Method for synthesizing benzyl alkyl disulfide

A technology for synthesizing benzyl alkyl disulfides and alkyl halides, which is applied in the field of synthesis of benzyl alkyl disulfides, can solve the problem that the asymmetric disulfide reaction has not been further explored, has a relatively irritating odor, It is not easy to scale production and other problems, to achieve the effect of saving energy consumption, low price and easy access

Inactive Publication Date: 2014-08-06
中国人民解放军63975部队
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (1) The thiol that provides the sulfur source in the reaction is a reagent that is not friendly to the environment and has a relatively pungent odor. It also causes certain potential toxicity to the human body and is not easy to scale production
[0006] (2) Organic solvents are more or less toxic and expensive, causing certain pollution to the environment
Recently, Firouzabadi et al. studied the reaction of thiourea to synthesize symmetrical disulfides, but the reaction of unsymmetrical disulfides was not further explored.

Method used

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  • Method for synthesizing benzyl alkyl disulfide
  • Method for synthesizing benzyl alkyl disulfide

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Preparation of Benzyl Octyl Disulfide

[0020] Benzyl thiocyanide 149mg (1mmol), 1-bromooctane 288mg (1.5mmol), thiourea 152mg (2mmol), potassium iodide 248mg (1.5mmol), tetrabutylammonium bisulfate 509mg (1.5mmol) and potassium phosphate 207mg (1.2mmol) added to 3mL H 2 In the reaction vial of O, the reaction temperature was set at 90°C and stirred by microwave. Set the reaction time to 15min, and stop the reaction when the time is over. The resultant was extracted with DCM, and the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product. Purified by silica gel column, eluent: n-hexane, and isolated to obtain benzyl octyl disulfide.

[0021] Benzyl octyl disulfide is a colorless oil with a yield of 61%.

[0022] GC-MS: [C 15 h 24 S 2 +H] + The calculated value of is 269.1319 and the measured value is 269.0130.

[0023] 1 H NMR (400MHz, CD 3 OD) δ: 7.38-7.14 (m, 5H), 3.88 (s, 2H), 2.34 (t, J=7....

Embodiment 2

[0026] Preparation of Benzyl Heptyl Disulfide

[0027] Benzyl thiocyanide 149mg (1mmol), 1-bromoheptane 267mg (1.5mmol), thiourea 152mg (2mmol), potassium iodide 248mg (1.5mmol), tetrabutylammonium bisulfate 509mg (1.5mmol) and potassium phosphate 207mg (1.2mmol) added to 3mL H 2 In the reaction vial of O, the reaction temperature was set at 90°C and stirred by microwave. Set the reaction time to 15min, and stop the reaction when the time is over. The resultant was extracted with DCM, and the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product. Through silica gel column purification, eluent: n-hexane, benzyl heptyl disulfide was isolated.

[0028] Benzylheptyl disulfide is a colorless oily substance with a yield of 88%.

[0029] GC-MS: [C 14 H2 2 S 2 +H] + The calculated value is 255.1163, and the measured value is 254.9696.

[0030] 1 H NMR (600MHz, CD 3 OD)δ: 7.37-7.26(m, 5H), 3.91(s, 2H), 2.39-...

Embodiment 3

[0033] Preparation of Benzyl Hexyl Disulfide

[0034] Benzyl thiocyanide 149mg (1mmol), 1-bromohexane 246mg (1.5mmol), thiourea 152mg (2mmol), potassium iodide 248mg (1.5mmol), tetrabutylammonium bisulfate 509mg (1.5mmol) and potassium phosphate 207mg (1.2mmol) added to 3mL H 2 In the reaction vial of O, the reaction temperature was set at 80 °C and stirred by microwave. Set the reaction time to 15min, and stop the reaction when the time is over. The resultant was extracted with DCM, and the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product. Purify by silica gel column, eluent: n-hexane, and isolate benzyl hexyl disulfide.

[0035] Benzylhexyl disulfide is a colorless oil with a yield of 85%.

[0036]GC-MS: [C 13 h 20 S 2 +H] + The calculated value of is 241.1006 and the measured value is 241.9353.

[0037] 1 H NMR (400MHz, CD 3 OD) δ: 7.35-7.23 (m, 5H), 3.88 (s, 1H), 2.35 (t, J = 7.3Hz, 2H), 1....

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Abstract

The invention relates to a method for synthesizing benzyl alkyl disulfide. Thiourea and benzyl thiocyanate taken as sulfur sources, alkyl halide taken as a raw material, potassium iodide and tetrabutylammonium hydrogen sulfate taken as catalysts, potassium phosphate taken as alkali react in water to obtain an asymmetric benzyl alkyl disulfide compound. According to the method, sulfur alcohol with pungent smell is prevented from being used as a sulfur source, and a microwave reaction technology and a one-pot method are adopted, so that the purposes of green and environmental protection can be achieved, the operational program is simplified, and the costs of synthesis and large-scale production are further reduced.

Description

technical field [0001] The invention relates to a synthesis method of benzyl alkyl disulfide. Background technique [0002] Disulfide compounds play a very important role in chemistry and biochemistry. All proteins contain disulfide bonds, and these disulfide bonds play a role in stabilizing the protein structure. Some target drug molecules with a series of biological activities contain disulfide bonds, such as anticancer active molecules. Therefore, the method of constructing asymmetric disulfide bonds has great reference value for the synthesis of biologically active peptides and peptidomers. [0003] At present, there are many methods for synthesizing symmetrical disulfides, but these methods are not universal for the synthesis of unsymmetrical disulfides, because the sulfide ion exchange is very fast, and it is easy to undergo self-reaction to obtain symmetrical disulfides. Recently, the study of unsymmetrical disulfides has attracted extensive attention, and a series...

Claims

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Application Information

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IPC IPC(8): C07C319/24C07C321/20C07C323/52
Inventor 王红梅卢晓刚高润利赵东媛孙道鸣
Owner 中国人民解放军63975部队
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