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A kind of tetraphenylphosphine amido derivative and its synthetic method

A technology for tetraphenylphosphine amido derivatives and its derivatives, which is applied in the field of tetraphenylphosphine amido derivatives and their synthesis, and can solve problems such as differences in bond-forming properties

Inactive Publication Date: 2016-08-24
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, although N and P belong to the same main group, their bonding properties are very different. For example, in tetraphenylphosphineamide, N is only connected to one benzene ring, while P is connected to three benzene rings at the same time.

Method used

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  • A kind of tetraphenylphosphine amido derivative and its synthetic method
  • A kind of tetraphenylphosphine amido derivative and its synthetic method
  • A kind of tetraphenylphosphine amido derivative and its synthetic method

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preparation example Construction

[0040] combine figure 1 , the synthetic method of the tetraphenyl phosphonium amide derivative of the present invention comprises the following steps:

[0041] (1) 5~20wt% hydrochloric acid is added to compound a for reaction, the reaction temperature is controlled at 0~20°C, and the chemical formula of compound a is stirred for 0.5~2h. Add 2-10 mL of hydrochloric acid per mole of compound a;

[0042] (2) Add 5~20wt% sodium nitrite aqueous solution to the above reaction solution, the molar ratio of compound a and sodium nitrite is 1:(1~2), the reaction temperature is controlled at 0~20°C, and stirred for 0.5~2h ;

[0043] (3) adding 5~20wt% sodium azide aqueous solution to above-mentioned reaction solution, the mol ratio of compound a and sodium azide is 1: (1~2), reaction temperature is controlled at 0~20 ℃, stirring 0.5-2h; through extraction, washing, drying, filtration, solvent removal, column chromatography or vacuum distillation to obtain intermediate b.

[0044] (4...

Embodiment 1

[0050] A class of tetraphenyl phosphonium amide derivatives of the present invention, its molecular structural formula is shown in the following formula:

[0051]

[0052] combine figure 2 , the synthetic method of the tetraphenyl phosphonium amide derivative of the present embodiment comprises the following steps:

[0053] (1) To 19.3 g of compound a1 ( ), add 1L of 5% hydrochloric acid, control the reaction temperature at 5°C, and stir for 1h;

[0054] (2) 100 mL of 10% sodium nitrite aqueous solution was added to the above reaction solution, the reaction temperature was controlled at 5°C, and stirred for 1 h;

[0055] (3) 100 mL of 8% sodium azide aqueous solution was added to the above reaction solution, the reaction temperature was controlled at 5 °C, and stirred for 1 h; after extraction, washing, drying, filtration, the solvent was removed, and the compound b1 was obtained by column chromatography. Compound b1 is the first intermediate of the present invention. ...

Embodiment 2

[0066] A class of tetraphenyl phosphonium amide derivatives of the present invention, its molecular structural formula is shown in the following formula:

[0067]

[0068] combine image 3 , the synthetic method of the tetraphenyl phosphonium amide derivative of the present embodiment comprises the following steps:

[0069] (1) To 19.3 g of compound a2 ( ), add 1L of 5% hydrochloric acid, control the reaction temperature at 5°C, and stir for 1h;

[0070] (2) 100 mL of 10% sodium nitrite aqueous solution was added to the above reaction solution, the reaction temperature was controlled at 5°C, and stirred for 1 h;

[0071] (3) 100 mL of 8% sodium azide aqueous solution was added to the above reaction solution, the reaction temperature was controlled at 5°C, and stirred for 1 h; after extraction, washing, drying, filtration, the solvent was removed, and column chromatography was used to obtain compound b2. Compound b2 is the first intermediate of the present invention. Th...

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Abstract

The invention discloses a tetraphenylphosphine amido derivative and a synthesis method thereof. The synthesis method of the tetraphenylphosphine amido derivatives of the invention has mild reaction conditions, short reaction time, and high conversion rate and yield. The synthesis method of the tetraphenylphosphine amido derivatives comprises the following steps: adding hydrochloric acid to compound a, stirring for a certain period of time, then adding an aqueous solution of sodium nitrite, continuing stirring for a certain period of time, then adding an aqueous solution of sodium azide, and reacting Complete separation and purification to obtain compound b; add n-butyllithium to compound c, stir for a certain period of time, then add phosphorus trihalide, continue stirring for a certain period of time, then add borane, extract, wash, dry, and filter after the reaction is complete , remove the solvent, add diethylamine, separate and purify after the reaction is complete to obtain compound d; react b and d to obtain tetraphenylphosphineamide derivatives. The tetraphenylphosphine amido derivatives can be used in the synthesis of important nitrogen-containing compounds such as guanidines and amidines, as well as in fields such as photoelectric materials.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a tetraphenylamine phosphine derivative and a synthesis method thereof. Background technique [0002] Due to the wide application of heteroatom-containing organic compounds in functional materials, biomedicine and other fields, the synthesis of such compounds has received extensive attention. Derivatives of tetraphenylphosphonium amide have been widely used to synthesize important nitrogen-containing compounds such as guanidines and amidines. At the same time, although N and P belong to the same main group, their bonding properties are quite different. For example, in tetraphenylphosphonium amide, N is only connected to one benzene ring, while P is connected to three benzene rings at the same time. Considering the difference in N,P electronegativity, the conjugated-extended tetraphenylphosphonium amide derivatives may have special spectral properties. SUM...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/50
Inventor 方敬坤俞宪杨鑫
Owner NANJING UNIV OF SCI & TECH