Synthesis method of N, N, N', N'-tetramethylchloroformamidinium hexafluorophosphate

A technology of tetramethylchloroformamidine and hexafluorophosphate, applied in the direction of organic chemistry, can solve the problems of reduced service life of production equipment, strong corrosion of hexafluorophosphoric acid, and high toxicity of oxalyl chloride, and achieve low production cost, Avoid severe corrosion and reduce the effect of service life

Inactive Publication Date: 2017-06-20
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Phosgene is a severe suffocating poisonous gas. Inhalation of high concentration can cause pulmonary edema. It is about 10 times more toxic than chlorine gas. Oxalyl chloride is also more toxic and can easily cause safet

Method used

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Examples

Experimental program
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Example Embodiment

[0019] Example 1

[0020] (1) Synthesis of tetramethyl chloroformamidine dichlorophosphate: add 0.086 mol of tetramethyl urea liquid to the reaction kettle, ice bath, when the system temperature reaches 0 ℃, add 0.086 mol of POCl dropwise 3 Liquid, the dripping time is 30 minutes. After the dripping is completed, the reaction kettle is moved to an oil bath, the temperature is raised to 100° C., the reaction is 60 minutes, and it is cooled to room temperature to obtain a transparent yellow liquid.

[0021] (2) Synthesis of N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate (TCFH): add 100mL of dichloromethane to the reaction solution obtained in step (1), and place it in an ice bath Under the conditions, use a peristaltic pump to add 200 mL of potassium hexafluorophosphate aqueous solution (the number of moles is 0.083 mol), the dripping time is 15 minutes, after the dripping is completed, continue to vigorously stir for 30 minutes under ice bath, separate the liquids, and us...

Example Embodiment

[0022] Example 2

[0023] (1) Synthesis of tetramethylchloroformamidine dichlorophosphate: add 0.086mol of tetramethylurea liquid into the reactor, when the system temperature reaches 20℃, add 0.097mol of POCl dropwise 3 Liquid, the dripping time is 45 minutes. After the dripping is completed, the reaction kettle is moved to an oil bath, the temperature is raised to 100° C., the reaction is 60 minutes, and it is cooled to room temperature to obtain a transparent yellow liquid.

[0024] (2) Synthesis of N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate (TCFH): Add 140mL of dichloromethane to the reaction solution obtained in step (1), and place it in an ice bath Under the conditions, use a peristaltic pump to add 200 mL of potassium hexafluorophosphate aqueous solution (the number of moles is 0.085 mol), the dripping time is 45 minutes, after the dripping, continue to vigorously stir for 30 minutes under the ice bath, separate the liquid, and use 200 mL to deionize The orga...

Example Embodiment

[0025] Example 3

[0026] (1) Synthesis of tetramethylchloroformamidine dichlorophosphate: add 0.086mol of tetramethylurea liquid to the reactor, when the system temperature reaches 5℃, add 0.086mol of POCl dropwise 3 Liquid, the dripping time is 30 minutes, the reaction kettle is moved to an oil bath, the temperature is raised to 100°C, the reaction is 60 minutes, and it is cooled to room temperature to obtain a transparent yellow liquid.

[0027] (2) Synthesis of N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate (TCFH): Add 180 mL of dichloromethane to the reaction solution obtained in step (1), and place it in an ice bath Under the conditions, use a peristaltic pump to drop 200 mL of potassium hexafluorophosphate aqueous solution (the number of moles is 0.086 mol), and the dripping time is 45 minutes. After the dripping is completed, continue to vigorously stir for 30 minutes in an ice bath, separate the liquids, and use 200 mL for deionization. The organic phase was wa...

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Abstract

The invention relates to a synthesis method of N, N, N', N'-tetramethylchloroformamidinium hexafluorophosphate (TCFH). The method includes: first subjecting phosphoryl chloride and tetramethylurea to chlorination reaction to generate tetramethylchloroformamidinium dichlorophosphate, then subjecting potassium hexafluorophosphate and tetramethylchloroformamidinium dichlorophosphate to chlorion exchange so as to obtain N, N, N', N'-tetramethylchloroformamidinium hexafluorophosphate. Compared with the traditional synthesis method, the method provided by the invention uses phosphoryl chloride to replace phosgene and oxalyl chloride to serve as a chlorinating agent, and employs potassium hexafluorophosphate to replace hexafluorophosphoric acid to serve as an ion exchange agent, has the characteristics of low toxicity and no pollution, etc., can effectively avoid the serious corrosion of hexafluorophosphoric acid to instrument and equipment and poisoning to the human body. The synthesis process is simple, the operation is safe and convenient, the product purity is high, and the cost is low.

Description

technical field [0001] The invention relates to a synthesis method of N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate, which belongs to the technical field of fine chemical preparation. Background technique [0002] N,N,N',N'-Tetramethylchloroformamidine hexafluorophosphate (TCFH) is a good non-hygroscopic coupling reagent for peptide synthesis, as well as a starting material for other coupling reagents. As a general activating reagent of solid-phase chemistry, TCFH mainly promotes the formation of carboxylic acid amine derivatives rather than amides during the coupling process of amino acids. It is very useful for the coupling of very hindered amino acids, and has the characteristics of simple and convenient synthesis process and long shelf life. Traditional TCFH preparation mainly involves the reaction of tetramethylurea and phosgene (carbonyl chloride) or oxalyl chloride in toluene to form tetramethylchloroformamide, followed by the exchange of chloride ions b...

Claims

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Application Information

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IPC IPC(8): C07C257/10
CPCC07C257/10
Inventor 刘洪杰张思思邢山川陆文超刘满超刘少杰
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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