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Method for synthesizing benzyl alkyl sulfur ether

A technology for synthesizing benzyl alkyl sulfide and alkyl halide, applied in the field of synthesis of benzyl alkyl sulfide, can solve the problems of unfriendly environment, toxicity, long reaction time and the like, shorten the reaction time and improve the yield. efficiency and cost reduction

Inactive Publication Date: 2014-04-30
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) Metal palladium, nickel and some phosphorus ligands are often used in metal catalyzed reactions, which may cause certain pollution to the environment
Kevin S.Eccles etc. synthesized a series of symmetrical and asymmetrical benzyl sulfides with thiourea, the yield is between 83-94%, but the reaction time of this kind of method is long

Method used

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  • Method for synthesizing benzyl alkyl sulfur ether
  • Method for synthesizing benzyl alkyl sulfur ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of benzyl dodecyl sulfide

[0023] Benzyl bromide 169mg (1mmol), 1-bromododecane 273mg (1.1mmol), thiourea 91mg (1.2mmol) and potassium carbonate 414mg (3mmol) are added in the reaction bottle that 5mLDMF is housed, and reaction temperature is set to 100°C, heating and stirring. The progress of the reaction was monitored by gas chromatography, and the reaction was stopped when the benzyl bromide was consumed. Naturally cooled to room temperature, concentrated and evaporated to remove the solvent, dissolved in dichloromethane, washed three times with water, combined organic phases, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product. Purify by silica gel column, eluent: n-hexane, and isolate benzyl dodecyl sulfide.

[0024] Benzyl dodecyl sulfide is a colorless oil with a yield of 87.6%.

[0025] GC-MS: C 19 h 32 S[M+H] + The calculated value of is 292.2225 and the measured value is 291.7474.

[0026] 1 H NMR (4...

Embodiment 2

[0029] Preparation of Benzyl Octyl Sulfide

[0030] 169 mg (1 mmol) of benzyl bromide, 249 mg (1.3 mmol) of 1-bromooctane, 91 mg (1.2 mmol) of thiourea and 414 mg (3 mmol) of potassium carbonate were added to a reaction flask containing 5 mL of DMF, and the reaction temperature was set to 100 ℃, heating and stirring. The progress of the reaction was monitored by gas chromatography, and the reaction was stopped when the benzyl bromide was consumed. Naturally cooled to room temperature, concentrated and evaporated to remove the solvent, dissolved in dichloromethane, washed three times with water, combined organic phases, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product. Purify by silica gel column, eluent: n-hexane, and isolate benzyl octyl sulfide.

[0031] Benzyl octyl sulfide is a colorless oil with a yield of 87.1%.

[0032] GC-MS: C 15 h 24 S[M+H] + The calculated value of is 236.1599 and the measured value is 235.9009.

[0...

Embodiment 3

[0036] Preparation of Benzyl Hexyl Sulfide

[0037] Add 169 mg (1 mmol) of benzyl bromide, 327 mg (2 mmol) of 1-bromohexane, 91 mg (1.2 mmol) of thiourea and 414 mg (3 mmol) of potassium carbonate to a reaction flask containing 5 mL of DMF, and set the reaction temperature to 100°C , heating and stirring. The progress of the reaction was monitored by gas chromatography, and the reaction was stopped when the benzyl bromide was consumed. Naturally cooled to room temperature, concentrated and evaporated to remove the solvent, dissolved in dichloromethane, washed three times with water, combined organic phases, 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 sulfide.

[0038] Benzylhexyl sulfide is a colorless oily substance with a yield of 92.3%.

[0039] GC-MS: C 12 h 20 S[M+H] + The calculated value is 208.1286, and the measured value is 207.8443.

[0040]...

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Abstract

The invention relates to a method for synthesizing benzyl alkyl sulfur ether. With thiourea as a sulfur source, benzyl bromide or benzyl halide reacts with alkyl alkyl halide under the catalysis effect of inorganic alkali to obtain an asymmetric benzyl alkyl sulfur ether compound. The method avoids the use of mercaptan with a pungent smell as the sulfur source, and adopts the one-pot method, so that the purpose of environmental protection can be achieved, and the operational program is simplified to further reduce the cost of synthesis and large-scale production.

Description

technical field [0001] The present invention relates to a kind of synthesis method of benzyl alkyl sulfide. Background technique [0002] There are many sulfur-containing organic compounds in nature, some of which play an important role in the treatment of our body diseases, such as penicillin, sulfonamides, cephalosporins, VB 1 Wait. Thioether compounds play an important role in biological processes and production and life. Akihiko et al. studied the biological activity of a series of benzyl phenyl sulfides and found that they have good antibacterial activity. Benzyl sulfide can also be used as an extreme pressure lubricant additive, a car oil anti-wear additive, and a photosensitive emulsion stabilizer. It is also used in the refining and recovery of precious metals and food preservation. [0003] The construction of C-S bonds is an indispensable tool for the synthesis of many thioether compounds with pharmaceutical activity. The traditional methods for constructing C-S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/06C07D239/38C07C319/14C07C321/20C07C321/22C07C323/16C07C323/07
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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