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Synthesizing method of 1-methyl-5-aminotetrazole

A technology of aminotetrazole and synthesis method, applied in directions such as organic chemistry, can solve the problems of many by-products, low reaction yield and the like, and achieve the effect of easy operation

Inactive Publication Date: 2013-10-16
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the by-product of this method is more, and reaction yield is lower

Method used

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  • Synthesizing method of 1-methyl-5-aminotetrazole
  • Synthesizing method of 1-methyl-5-aminotetrazole
  • Synthesizing method of 1-methyl-5-aminotetrazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 20ml of distilled water and 15.4g of 5-aminotetrazole monohydrate into a 250ml three-neck flask to form a suspension. Under stirring at 20°C to 25°C, add 89ml of aqueous sodium hydroxide solution with a mass concentration of 7.0% into the three-necked flask, and stir to dissolve 5-aminotetrazole monohydrate. Mix 9.8g of dimethyl sulfate with 20ml of toluene, add the toluene liquid containing dimethyl sulfate into the three-necked flask under stirring at 20°C~25°C, heat up to 88°C~89°C while stirring, and react for 1.5 hours , cooled to room temperature, the reaction solution was left to stand, and the water phase was separated. After about 70ml of water was evaporated under reduced pressure, the water phase after part of the water was evaporated under reduced pressure was cooled to 0 ° C ~ 3 ° C, filtered, and the obtained solid was filtered with 0 The solid was washed with 5 ml of cold water at ℃~3℃, and dried at room temperature to obtain a crude product. Accordi...

Embodiment 2

[0035] Add 20ml of distilled water and 15.4g of 5-aminotetrazole monohydrate into a 250ml three-neck flask to form a suspension. Under stirring at 20°C to 25°C, add 83ml of aqueous sodium hydroxide solution with a mass concentration of 7.5% into the three-necked flask, and stir to dissolve 5-aminotetrazole monohydrate. Mix 9.8g of dimethyl sulfate with 60ml of xylene, add the xylene liquid containing dimethyl sulfate into the three-necked flask under stirring at 20°C to 25°C, heat up to 92°C to 93°C while stirring, and react After 2.5 hours, cool to room temperature, let the reaction solution stand still, separate the water phase, evaporate about 70ml of water under reduced pressure, cool the water phase after removing part of the water under reduced pressure to 0°C-3°C, filter, and filter the obtained solid, The solid was washed with 5 ml of cold water at 0°C to 3°C, and dried at room temperature to obtain a crude product. According to NMR analysis, 1-methyl-5-aminotetrazole...

Embodiment 3

[0037]Add 20ml of distilled water and 15.4g of 5-aminotetrazole monohydrate into a 250ml three-neck flask to form a suspension. Under stirring at 20°C to 25°C, add 87ml of aqueous sodium hydroxide solution with a mass concentration of 7.2% into the three-necked flask, and stir to dissolve 5-aminotetrazole monohydrate. Mix 9.8g dimethyl sulfate with 100ml mixed solvent (toluene: chlorobenzene=1:1, v / v), mix the mixed solvent of toluene and chlorobenzene containing dimethyl sulfate under stirring at 20℃~25℃ Add the liquid into the three-necked flask, heat it up to 91°C to 93°C under stirring, react for 4.5 hours, cool to room temperature, let the reaction liquid stand still, separate the water phase, and evaporate about 70ml of water under reduced pressure, and then remove part of the water under reduced pressure The final aqueous phase was cooled to 0°C-3°C, filtered, and the obtained solid was filtered, washed with 5ml of cold water at 0°C-3°C, and dried at room temperature to...

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Abstract

The invention discloses a synthesizing method of 1-methyl-5-aminotetrazole. According to the method, 5-aminotetrazole monohydrate is adopted as a raw material, and is added into a reaction bottle with distilled water; under stirring under a temperature of 20-25 DEG C, a sodium hydroxide water solution with a mass concentration of 7.0-7.5% is added; under stirring under a temperature of 20-25 DEG C, an organic solvent comprising dimethyl sulfate is added; the material is heated to a temperature of 88-93 DEG C, and a reaction is carried out for 1.5-4.5h; such that the 1-methyl-5-aminotetrazole compound is obtained. A molar ratio of 5-aminotetrazole monohydrate to dimethyl sulfate is 1:0.52. A mass volume ratio of dimethyl sulfate to the organic solvent is 1:2.0-10.2. The organic solvent is toluene, xylene or chlorobenzene, or a mixed solvent of toluene and chlorobenzene with a volume ratio of 1:1. The method is simple to operate. The alkalinity of the reaction liquid is not needed to be repeatedly regulated during reaction. A reaction yield is high, and byproduct is less.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of 1-methyl-5-aminotetrazole. Background technique [0002] 1-methyl-5-aminotetrazole is an important energetic material intermediate and pharmaceutical intermediate. At present, the synthesis method of 1-methyl-5-aminotetrazole is generally to methylate 5-aminotetrazole change. However, the by-product of 2-methyl-5-aminotetrazole is easily produced during the methylation process, resulting in a low yield of 1-methyl-5-aminotetrazole. For example, Robert J.Spear disclosed in "Positional Selectivity of the Methylation of 5-Substituted Tetrazolate Anions" (Aust.J.Chem., 1984, 37, 2453-2468) the methylation of a series of 5-substituted tetrazolate compounds , analyze the crude product with nuclear magnetic resonance, measure the ratio of 2-position methylation product to 1-position methylation product, and then study the methylation law. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/06
Inventor 石强唐望秦明娜吕英迪姜俊张彦陈志强李洪丽郑晓东邱少君王民昌郭涛刘敏
Owner XIAN MODERN CHEM RES INST
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