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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 safety accidents.
In addition, hexafluorophosphoric acid is highly corrosive and can be toxic to the body if inhaled, in contact with the skin and swallowed, and can significantly reduce the service life of production equipment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1) Synthesis of tetramethylchloroformamidine dichlorophosphate: Add 0.086mol of tetramethylurea liquid into the reaction kettle, put it in an ice bath, and add 0.086mol of POCl dropwise when the system temperature reaches 0°C 3 Liquid, the dropwise addition time is 30 minutes. After the dropwise addition is completed, move the reactor to an oil bath, heat up to 100°C, react for 60 minutes, and cool 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 in an ice bath Under certain conditions, use a peristaltic pump to add 200mL of potassium hexafluorophosphate aqueous solution (0.083mol in moles) dropwise for 15 minutes. The organic phase was washed three times with ionized water, separated again, dried with magnesium sulfate, rotary evaporated at 50°C, crystallized, and dried to obtain a ...

Embodiment 2

[0023] (1) Synthesis of tetramethylchloroformamidine dichlorophosphate: Add 0.086mol of tetramethylurea liquid into the reaction kettle, and add 0.097mol of POCl dropwise when the system temperature reaches 20°C 3 Liquid, the dropwise addition time is 45 minutes. After the dropwise addition, move the reactor to an oil bath, raise the temperature to 100°C, react for 60 minutes, and cool to room temperature to obtain a transparent yellow liquid.

[0024] (2) Synthesis of N,N,N',N'-tetramethylchloroformamidine hexafluorophosphate (TCFH): Add 140 mL of dichloromethane to the reaction solution obtained in step (1), and place in an ice bath Under certain conditions, use a peristaltic pump to add 200mL potassium hexafluorophosphate aqueous solution (molar number is 0.085mol) dropwise, and the dropwise addition time is 45 minutes. Wash the organic phase with water three times, separate the liquid again, dry the organic phase with magnesium sulfate, rotary evaporate the organic phase a...

Embodiment 3

[0026] (1) Synthesis of tetramethylchloroformamidine dichlorophosphate: Add 0.086mol of tetramethylurea liquid into the reaction kettle, and add 0.086mol of POCl dropwise when the system temperature reaches 5°C 3 Liquid, the dropping time is 30 minutes. Move the reactor to an oil bath, raise the temperature to 100°C, react for 60 minutes, and cool 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 in an ice bath Under certain conditions, use a peristaltic pump to add 200mL potassium hexafluorophosphate aqueous solution (mole number is 0.086mol) dropwise for 45 minutes. Wash the organic phase with water three times, separate the liquid again, dry the organic phase with magnesium sulfate, rotary evaporate the organic phase at 50°C, crystallize and dry to obtain a white solid with a yield of 61....

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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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