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Method for preparing 1-benzyl-4- benzylthiomethyl-pyridinium iodide

A technology of benzylthio and pyridinium salts, which is applied in the field of preparation of 1-benzyl-4-thiobenzyl-pyridinium salt iodide, which can solve the strong toxicity of benzyl halides, the difficulty of obtaining synthetic raw materials, and the strong corrosion of benzylamine To achieve the effect of high product purity, low cost and reduced toxicity

Inactive Publication Date: 2012-08-15
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The synthetic raw materials of the above two compounds are not easy to obtain, and the raw material benzylamine has strong corrosiveness and benzyl halide has extremely strong toxicity

Method used

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  • Method for preparing 1-benzyl-4- benzylthiomethyl-pyridinium iodide
  • Method for preparing 1-benzyl-4- benzylthiomethyl-pyridinium iodide
  • Method for preparing 1-benzyl-4- benzylthiomethyl-pyridinium iodide

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Embodiment 1

[0039] Embodiment one, see appendix figure 1 , the preparation method of 1-benzyl-4-thiobenzyl-pyridinium iodide, comprises the following steps:

[0040] (1) 0.10 mmol iodine (I 2 ), 0.10 mmol of 4-mercaptopyridine, 1.0 mmol of benzyl alcohol and 3 microliters of water were mixed in 2 milliliters of acetonitrile, and reacted for 1000 to 7000 minutes at 100° C. to 150° C. under solvothermal reaction conditions. The preferred condition is to react for 2000 minutes under solvothermal reaction conditions of 150°C.

[0041] (2) Then slowly lower the temperature to obtain an orange-red mother liquor containing 1-benzyl-4-thiobenzyl-pyridinium iodide. The mother liquor was mixed with 10 ml of diethyl ether to obtain a light pink crystalline product of 1-benzyl-4-thiobenzyl-pyridinium iodide. If 10 milliliters of ether is carefully covered on the mother liquor, and the two liquid phases are slowly diffused with each other, a purple-red long flaky single crystal of 1-benzyl-4-thiobe...

Embodiment 2

[0045] Embodiment two: see attached figure 2 , using 1-benzyl-4-thiobenzyl-pyridinium iodide for the synthesis of functional metal complexes, comprising the following steps:

[0046] (1) Mix 0.10 mmol of silver iodide, 0.10 mmol of potassium iodide and 0.10 mmol of 1-benzyl-4-thiobenzyl-pyridinium iodide in 2 ml of acetonitrile, and react for 2000 minutes at 150°C under solvothermal reaction conditions ;

[0047] (2) then slowly cool down to obtain yellow needle-like crystals {[(C19 h 18 NS)(AgI 2 )] n}. Its single crystal structure is figure 2 As shown, the anion part is one-dimensional (AgI 2 ) n chain.

[0048] (3) the crystalline product is enriched by filtration, washed three times with two milliliters of ethyl acetate respectively, and dried at normal temperature to obtain high-purity crystalline {[(C 19 h 18 NS)(AgI 2 )] n}product. Yield: 66%.

[0049] (4) Elemental analysis: theoretical value (C 19 h 18 NSAgI 2 ): C, 34.89; H, 2.77; N, 2.14. Found: ...

Embodiment 3

[0051] Embodiment three, see appendix figure 1 , the preparation method of 1-benzyl-4-thiobenzyl-pyridinium iodide, comprises the following steps:

[0052] (1) 0.10 mmol iodine (I 2 ), 0.10 mmol of 4-mercaptopyridine, 1.0 mmol of benzyl alcohol and 3 microliters of water were mixed in 2 milliliters of acetonitrile, and reacted for 3000 minutes at 140 ° C under solvothermal reaction conditions.

[0053] (2) Then slowly lower the temperature to obtain an orange-red mother liquor containing 1-benzyl-4-thiobenzyl-pyridinium iodide. The mother liquor was mixed with 10 ml of diethyl ether to obtain a light pink crystalline product of 1-benzyl-4-thiobenzyl-pyridinium iodide. If 10 milliliters of ether is carefully covered on the mother liquor, and the two liquid phases are slowly diffused with each other, a purple-red long flaky single crystal of 1-benzyl-4-thiobenzyl-pyridinium salt iodide can be obtained after one week. Its single crystal structure (C 19 h 18 NS) (I) such as ...

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Abstract

The invention discloses a method for preparing 1-benzyl-4- benzylthiomethyl-pyridinium iodide, comprising the following steps of: mixing molecular iodine, 4-mercaptopyridine, benzyl alcohol and little water into acetonitrile to react for 1000-7000 minutes under a solvent-thermal condition at the temperature of 100-150 DEG C to prepare 1-benzyl-4- benzylthiomethyl-pyridinium iodide, and then precipitating the 1-benzyl-4- benzylthiomethyl-pyridinium iodide by using a gradient cooling method. As the invention adopts the benzyl alcohol instead of benzyl chloride to be used as the benzylation reagent, the toxicity during synthesis is lowered. The method has higher yield between 70 percent and 80 percent, and the final product is in a crystalline state with high purity. In addition, the invention has simple device, simple method, low price, easy availability of raw materials and low cost, and does not need the protection of inert gases during reaction.

Description

technical field [0001] The invention relates to a nitrogen-containing onium salt compound and a sulfide compound, in particular to a preparation method of 1-benzyl-4-thiobenzyl-pyridinium iodide. Background technique [0002] Nitrogen-containing onium salt compounds are often used as phase transfer catalysts, photoinitiators, and surfactants. In the prior art, the preparation method of nitrogen-containing onium salt compounds is mainly through halogenated hydrocarbons and nitrogen-containing compounds with potential onium salts. The disadvantage of this method is that halogenated hydrocarbons are relatively toxic. [0003] Thioether compounds are another important reaction raw material and reagent in the chemical industry. In the prior art, there are three main methods for preparing thioether compounds: [0004] (1) Prepared by the alkylation reaction of mercaptan: [0005] R-Br+HS-R'→R-S-R'+HBr [0006] Alkali can catalyze this kind of reaction, and the mechanism is to g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/70
Inventor 郎建平陈阳杨舟郭承鑫倪春燕
Owner SUZHOU UNIV
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