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N-(2-benzimidazolemethyl) imidodimethyl phosphonic acid synthesis method

A technology of iminobismethylphosphonic acid and benzimidazolylmethyl, which is applied in the field of synthesis of N-iminobismethylphosphonic acid [imino bis], can solve the problem of difficult purification and 2-benzimidazolylmethyl base) amine is more expensive, low yield and other problems, to achieve the effect of easy to obtain synthetic raw materials, cheap synthetic raw materials, and simple purification methods

Inactive Publication Date: 2008-01-02
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 1. High cost
This method starting material (2-benzimidazolyl methyl) amine is more expensive, is difficult to obtain
[0006] 2. Many by-products, difficult to purify
[0007] 3. Low yield
The yield is only 17.3%

Method used

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  • N-(2-benzimidazolemethyl) imidodimethyl phosphonic acid synthesis method

Examples

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Embodiment 1

[0024] The synthesis of embodiment 1.N-(2-benzimidazolyl methyl) iminobismethylphosphonic acid

[0025]

[0026] Mix N-(carboxymethyl) iminobismethyl sulfonic acid (20mmol, 5.26g) and o-phenylenediamine (20mmol, 2.16g) in a 100ml open round-bottomed flask, Heat in a bath. After about 2 hours, no more water vapor came out indicating the reaction was complete. Cool the reactant to about 100°C, add 10ml of 5mol·L -1 hydrochloric acid, and the mixture was refluxed in an oil bath at 120°C for 2 hours. The reaction solution was completely evaporated to dryness with a rotary evaporator, 20ml of distilled water was added thereto, KOH solid was added in batches until a clear solution with pH=5 was formed, activated carbon was added to reflux for 0.5 hours, and an orange-yellow clear solution was obtained by filtration after cooling. Slowly add 6mol L dropwise to the solution -1 hydrochloric acid with constant stirring until the pH of the mixture was ≤ 1.0, during which a large a...

Embodiment 2

[0028] The synthesis of embodiment 2.N-(2-benzimidazolyl methyl) iminobismethylphosphonic acid

[0029] Mix N-(carboxymethyl)iminobismethyl-acid (20mmol, 5.26g) and o-phenylenediamine (20mmol, 2.16g) in a 100ml open round-bottomed flask, Heat in a bath. After about 3 hours, no more water vapor came out indicating the reaction was complete. The reactant was cooled to about 100°C, and 8ml of 7mol·L -1 hydrochloric acid, and the mixture was refluxed in an oil bath at 120°C for 2 hours. The reaction solution was completely evaporated to dryness with a rotary evaporator, 16ml of distilled water was added thereto, KOH solid was added in batches until a clear solution with pH=6 was formed, activated carbon was added to reflux for 0.5 hours, and an orange-yellow clear solution was obtained by filtration after cooling. Slowly add 6mol.L dropwise to the solution -1 hydrochloric acid with constant stirring until the pH of the mixture was ≤ 1.0, during which a large amount of white pr...

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Abstract

The synthesis process of N-(2-benzoimidazol methyl) imino dimethyl phosphonic acid includes the following steps: mixing and grinding N-(carboxyl methyl) imino dimethyl phosphonic acid and o-diaminobenzene in the same amount, reacting at 180-200 deg.c in an oil bath until no further bubbling water vapor, cooling, adding hydrochloric acid, refluxing, evaporating to eliminate solvent, adding distilled water, adding KOH until obtaining pH 5-6 clear liquid, adding active carbon and refluxing for 0.5 hr, cooling and filtering to obtain orange clear solution, dropping hydrochloric acid via stirring until reaching pH not higher than 1.0, filtering to obtain precipitate, refluxing the precipitate in methanol for 1 hr, cooling, filtering, washing and drying to obtain white N-(2-benzoimidazol methyl) imino dimethyl phosphonic acid crystal. The process has the advantages of cheap material, simple production purification and high yield.

Description

technical field [0001] The invention relates to a synthesis method of N-(2-benzoimidazolylmethyl)iminobismethylphosphonic acid [(Benzmidazol-2-ylmethyl)imino bis(methylenephophonic acid)]. Background technique [0002] U.S. Patent [Yoshikawa, K.Heterocyclic Iminobismethylenebisphosphonic AcidDerivatives.U.S.Patent 5,441,945,1995] reported N-(2-benzimidazolyl methyl) iminobismethylphosphonic acid [(Benzmidazol-2-ylmethyl)imino bis(methylenephophonic acid)] synthetic method: [0003] [0004] This method has the following disadvantages: [0005] 1. High cost. The starting material of this method (2-benzimidazolylmethyl) amine is relatively expensive and difficult to obtain. [0006] 2. Many by-products are difficult to purify. The crude product needs to be purified by ion exchange column. [0007] 3. Low yield. The yield is only 17.3%. Contents of the invention [0008] The object of the present invention is to provide a kind of synthetic method of N-(2-benzimidazo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6506
Inventor 郑丽敏曹登科
Owner NANJING UNIV
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