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Method for synthesizing methoxamine hydrochloride

A technology of methoxyamine hydrochloride and hydroxylamine hydrochloride is applied in the field of compound synthesis to achieve the effects of good atom economy, reduction of side reactions, and improvement of product yield and quality

Active Publication Date: 2012-01-04
JIANGSU QINGQUAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still the following defects: one is that ethyl acetate itself is saponified and hydrolyzed in the oximation process, so the theoretical conditions in the literature are difficult to realize; the other is that methoxyamine itself is unstable, and dimethyl sulfate is also easily hydrolyzed, so methyl If the pH value is too high, there are many side reactions, resulting in a decrease in yield; the third is to use vacuum distillation for impurity removal and purification, one is incomplete, and the other is that distillation at elevated temperature can easily lead to side reactions

Method used

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  • Method for synthesizing methoxamine hydrochloride
  • Method for synthesizing methoxamine hydrochloride
  • Method for synthesizing methoxamine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Add 10.6g (0.12mol) ethyl acetate and 7.0g (0.10mol) hydroxylamine hydrochloride into a 100mL flask equipped with electric stirring, thermometer and condenser, cool to 10℃, and start adding 40g NaOH with a mass fraction of 20% dropwise. (0.2mol) aqueous solution, drip for 1h, and react at 15°C for 0.5h after dripping. Then, 15.1g (0.12mol) of dimethyl sulfate was added dropwise at this temperature, and then the temperature was raised to 70°C for 4h. Cool to 10°C, add 200 mL of cold water, then extract three times with 100 mL of chloroform, and combine the extracts. The solvent was evaporated under reduced pressure (0.05MPa) at 30°C, the distillation residue was added to 17g of hydrochloric acid with a mass fraction of 15%, the temperature was raised to 65°C, and the temperature was kept for 0.5h. Then cool to 10°C, add dropwise 30% sodium hydroxide solution at no higher than this temperature to adjust the pH to 11, and then use heating distillation to collect the distil...

Embodiment 2

[0044] The amount of ethyl acetate was changed to 0.14 mol, and the others were the same as in Example 1. The result was 7.5 g of methoxyamine hydrochloride, the yield was 89.8%, and the product mole fraction was 99.2%.

Embodiment 3

[0046] For oximation, 24 g of 25% NaOH (0.15 mol) solution was added dropwise, and the others were the same as in Example 1. The result was 7.2 g of methoxyamine hydrochloride, the yield was 86.2%, and the product mole fraction was 98.6%. .

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Abstract

The invention provides a method for synthesizing methoxyamine hydrochloride and includes the following steps: ethyl acetate and hydroxylamine hydrochloride are added into a reaction vessel and 10 to 30 percent of sodium hydroxide solution is instilled for oximation reaction; then dimethyl sulfate is instilled, and at the same time sodium hydroxide solution with the mass fractions of 10 to 30 percent is instilled for methylation reaction; cold water is added after the temperature is decreased and a halohydrocarbon solvent is adopted for extraction; pressure is reduced under the temperature of 30 to 50 DEG C to recover the halohydrocarbon solvent and the product obtained is added into inorganic acid solution for hydrolysis reaction; after the hydrolysis is over, hydrochloride is used to obtain the product methoxyamine hydrochloride. The synthetic method which is simple improves the operation environment and increases the yield ratio.

Description

technical field [0001] The invention relates to the field of compound synthesis methods, in particular to a method for synthesizing methoxyamine hydrochloride. Background technique [0002] Methoxyamine hydrochloride, also known as o-methylarginine hydrochloride, is an important chemical product and pharmaceutical intermediate, such as it can be used for color photography and film printing; it is used as a reducing agent in the organic synthesis industry to prepare oximes; in medicine Used in the production of sulfamethoxazole, ethinoxazole, hydroxyurea, cefuroxime, etc. The methods currently used for the synthesis of methoxyamine hydrochloride are: [0003] Ji Yongxin (Chemistry and Adhesion, 2001, 5, 200-202) introduced such a synthetic route: use sodium bisulfite and sulfur dioxide to react with sodium nitrite to first form hydroxylamine sodium sulfite, and then form hydroxylamine sodium sulfite through methylation, hydrolysis, and neutralization. Salt produces product...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C239/20
Inventor 邵建华朱兆火冯珍会烫廷翔应海芬李伟朱学志
Owner JIANGSU QINGQUAN CHEM CO LTD
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