Preparation method of N-(3,4-dichlorobenzyl)hexamethylene tetra-ammonium chloride

Abstract

The invention discloses a preparation method of N-(3,4-dichlorobenzyl)hexamethylene tetra-ammonium chloride. The method comprises the following steps: adding hexamethylene tetra-amine into an organic solvent, stirring at room temperature, adding 3,4-dichlorobenzyl chloride in the stirring process, heating until the reaction is finished, stirring to cool and crystallize, filtering, washing and drying to obtain the N-(3,4-dichlorobenzyl)hexamethylene tetra-ammonium chloride, wherein the organic solvent is any one or two of ethyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, sec-butyl acetate, tert-butyl acetate, n-amyl acetate, isoamyl acetate or propyl propionate. The yield is stable and can reach above 90 percent, the step of removing the solvent is not related, further purification is not needed, aftertreatment is simple, and a product with the purity being above 99 percent can be obtained through direct washing and filtering. Amplification effect is avoided, the solvent cost is low, and the preparation method of the N-(3,4-dichlorobenzyl)hexamethylene tetra-ammonium chloride is particularly suitable for industrialized production.

Description

technical field

[0001] The invention relates to a preparation method, in particular to a preparation method of N-(3,4-dichlorobenzyl)hexamethylene tetraammonium chloride. It belongs to the field of medical technology. Background technique

[0002] N-(3,4-dichlorobenzyl)hexamethylenetetraammonium chloride is a raw material for the synthesis of 3,4-dichlorobenzylamine, and 3,4-dichlorobenzylamine is the synthesis of 1- A key intermediate of (3,4-dichlorobenzyl)-5-octylbiguanide (Olanexidine). Alkylguanidines have biological activity and are often used as agricultural fungicides and disinfectants. Alkylguanidine disinfectants are easily soluble in water and easy to use because they are made into salts. At the same time, due to their broad-spectrum antibacterial and low toxicity, their bactericidal scope is becoming wider and wider. They are not only used for surface disinfection in hospitals, In addition to disinfection in the food and alcoholic beverage industry, it is also...

Examples

Embodiment 1

[0026] Embodiment 1 (single ester solvent):

[0027] Add 74.9g of hexamethylenetetramine (urotropine) (534.6mmol, 1.1eq) into 475mL of ethyl acetate, and add 95g of 3,4-dichlorobenzyl chloride (486mmol, 1.0eq) under stirring at room temperature , then heated to 75°C, reacted for 6 hours, stopped heating, stirred and cooled to crystallize, filtered, washed with ethyl acetate, and dried in vacuum at 50°C for 4 hours to obtain 154.6g of N-(3,4-dichlorobenzyl)hexamethylene Methyltetraammonium chloride (white powdery solid), yield 94.8%, purity 99.6%, solvent residue 72ppm.

Embodiment 2

[0028] Embodiment 2 (single ester solvent):

[0029] Add 74.9g of hexamethylenetetramine (urotropine) (534.6mmol, 1.1eq) into 475mL of isopropyl acetate, stir at room temperature, add 95g of 3,4-dichlorobenzyl chloride (486mmol, 1.0eq ), then heated to 75°C, reacted for 6 hours, stopped heating, stirred and cooled to crystallize, filtered, washed with isopropyl acetate, and dried in vacuum at 50°C for 4 hours to obtain 151.4g N-(3,4-dichlorobenzyl) Hexamethylenetetraammonium chloride (white powdery solid), yield 92.8%, purity 99.3%, solvent residue 94ppm.

Embodiment 3

[0030] Embodiment 3 (single ester solvent):

[0031] Add 74.9g of hexamethylenetetramine (urotropine) (534.6mmol, 1.1eq) into 475mL of n-butyl acetate, stir at room temperature, add 95g of 3,4-dichlorobenzyl chloride (486mmol, 1.0eq ), then heated to 75°C, reacted for 6 hours, stopped heating, stirred and cooled to crystallize, filtered, washed with n-butyl acetate, and dried in vacuum at 50°C for 4 hours to obtain 149.3g N-(3,4-dichlorobenzyl) Hexamethylenetetraammonium chloride (white powdery solid), yield 91.5%, purity 99.1%, solvent residue 102ppm.

technical field

[0001] The invention relates to a preparation method, in particular to a preparation method of N-(3,4-dichlorobenzyl)hexamethylene tetraammonium chloride. It belongs to the field of medical technology. Background technique

[0002] N-(3,4-dichlorobenzyl)hexamethylenetetraammonium chloride is a raw material for the synthesis of 3,4-dichlorobenzylamine, and 3,4-dichlorobenzylamine is the synthesis of 1- A key intermediate of (3,4-dichlorobenzyl)-5-octylbiguanide (Olanexidine). Alkylguanidines have biological activity and are often used as agricultural fungicides and disinfectants. Alkylguanidine disinfectants are easily soluble in water and easy to use because they are made into salts. At the same time, due to their broad-spectrum antibacterial and low toxicity, their bactericidal scope is becoming wider and wider. They are not only used for surface disinfection in hospitals, In addition to disinfection in the food and alcoholic beverage industry, it is also...

Examples

Embodiment 1

[0026] Embodiment 1 (single ester solvent):

[0027] Add 74.9g of hexamethylenetetramine (urotropine) (534.6mmol, 1.1eq) into 475mL of ethyl acetate, and add 95g of 3,4-dichlorobenzyl chloride (486mmol, 1.0eq) under stirring at room temperature , then heated to 75°C, reacted for 6 hours, stopped heating, stirred and cooled to crystallize, filtered, washed with ethyl acetate, and dried in vacuum at 50°C for 4 hours to obtain 154.6g of N-(3,4-dichlorobenzyl)hexamethylene Methyltetraammonium chloride (white powdery solid), yield 94.8%, purity 99.6%, solvent residue 72ppm.

Embodiment 2

[0028] Embodiment 2 (single ester solvent):

[0029] Add 74.9g of hexamethylenetetramine (urotropine) (534.6mmol, 1.1eq) into 475mL of isopropyl acetate, stir at room temperature, add 95g of 3,4-dichlorobenzyl chloride (486mmol, 1.0eq ), then heated to 75°C, reacted for 6 hours, stopped heating, stirred and cooled to crystallize, filtered, washed with isopropyl acetate, and dried in vacuum at 50°C for 4 hours to obtain 151.4g N-(3,4-dichlorobenzyl) Hexamethylenetetraammonium chloride (white powdery solid), yield 92.8%, purity 99.3%, solvent residue 94ppm.

Embodiment 3

[0030] Embodiment 3 (single ester solvent):

[0031] Add 74.9g of hexamethylenetetramine (urotropine) (534.6mmol, 1.1eq) into 475mL of n-butyl acetate, stir at room temperature, add 95g of 3,4-dichlorobenzyl chloride (486mmol, 1.0eq ), then heated to 75°C, reacted for 6 hours, stopped heating, stirred and cooled to crystallize, filtered, washed with n-butyl acetate, and dried in vacuum at 50°C for 4 hours to obtain 149.3g N-(3,4-dichlorobenzyl) Hexamethylenetetraammonium chloride (white powdery solid), yield 91.5%, purity 99.1%, solvent residue 102ppm.

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