O-substituted hydroxylamine hydrochloride and preparation method thereof

A hydroxylamine hydrochloride and substituent technology, applied in the field of O-substituted hydroxylamine hydrochloride and its preparation, can solve the problems of preparing O-sulfonylhydroxylamine hydrochloride, having too much waste acid, being unsuitable for industrial production, and the like, and achieving The effect of short reaction time, high yield and high versatility

Active Publication Date: 2018-09-14
SUZHOU HIGHFINE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Method 4: The O-sulfonyl acetone oxime obtained by reacting acetone oxime with the corresponding sulfonyl chloride needs to be hydrolyzed with concentrated hydrochloric acid, and the sulfonate is easily hydrolyzed by strong acid, so this method cannot be used to prepare O-sulfonyl hydroxylamine hydrochloride , and this method has more waste acid, which is not suitable for industrial production

Method used

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  • O-substituted hydroxylamine hydrochloride and preparation method thereof
  • O-substituted hydroxylamine hydrochloride and preparation method thereof
  • O-substituted hydroxylamine hydrochloride and preparation method thereof

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preparation example Construction

[0032] Such as figure 1 As shown, the preparation method of O-substituted hydroxylamine hydrochloride according to the embodiment of the present invention includes:

[0033] Step S1, adding sodium hydroxide to the ethanol solution of ethyl acetylhydroxamic acid, and simultaneously adding halogenated hydrocarbons, sulfonyl chlorides or acid chlorides dropwise until the reaction is complete, adding the reactant to water to precipitate O-substituted acetylhydroxamic acid ethyl ester.

[0034] Specifically, the molar ratio of ethyl acetylhydroxamate: sodium hydroxide: halogenated hydrocarbon or sulfuryl chloride or acid chloride is 1:(1.1-1.5):(1.2-1.5).

[0035] Further, the substituent on the oxygen is an alkyl group or an acyl group.

[0036] When the substituent on the oxygen is an alkyl group, add a halogenated hydrocarbon to the ethanol solution of ethyl acetylhydroxamate, wherein the halogenated hydrocarbon can be bromoethane, 2-bromopropane, 3-bromopropene, tert-butyl O...

Embodiment 1

[0066] (1) Preparation of compound O-allyl acetylhydroxamate ethyl ester

[0067] Take a 1L reaction bottle and add ethyl acetylhydroxamate (142g, 1.0mol, 1.0eq) and ethanol (426mL, 3P) to form an ethanol solution of ethyl acetylhydroxamate, and add it to the ethanol solution of ethyl acetylhydroxamate Add sodium hydroxide (44g, 1.1mol, 1.1eq), then dropwise add 3-bromopropene (145.2g, 1.2mol, 1.2eq), magnetically stir to speed up the reaction, control the reaction temperature between 15-25°C, add dropwise Complete and keep the temperature between 15-25°C for 2 hours, add the reaction solution to water (426mL, 3P), filter the precipitated solid with suction, wash the obtained filter cake with ethanol, dry the obtained solid to obtain 154.85gO - Ethyl allyl acetyl hydroxamate, the yield is 85%.

[0068] (2) Preparation of compound O-allyl hydroxylamine hydrochloride

[0069] Add ethyl O-allyl acetylhydroxamate (154.85g, 0.85mol, 1eq) into a solution of 3mol / L hydrochloric aci...

Embodiment 2

[0073] (1) Preparation of compound O-tert-butyl acetylhydroxamate ethyl ester

[0074] Take a 1L reaction bottle and add ethyl acetylhydroxamate (142g, 1.0mol, 1.0eq) and ethanol (426mL, 3P) to prepare an ethanol solution of ethyl acetylhydroxamate, and add it to the ethanol solution of ethyl acetylhydroxamate Add sodium hydroxide (44g, 1.1mol, 1.1eq), then dropwise add tert-butyl bromide (164.4g, 1.2mol, 1.2eq), magnetically stir to speed up the reaction, control the reaction temperature between 15-25°C, add dropwise After the completion of the reaction, keep the temperature between 15-25°C for 2 hours, add the reaction liquid to water (426mL, 3P), filter the precipitated solid with suction, wash the filter cake with ethanol, and dry the obtained solid to obtain 169.85g O- Ethyl tert-butyl acetylhydroxamate, the yield is 85.7%.

[0075] (2) Preparation of compound O-tert-butylhydroxylamine hydrochloride

[0076] Add ethyl O-alkyl substituted acetylhydroxamate (169.85g, 0.85...

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Abstract

The invention provides O-substituted hydroxylamine hydrochloride and a preparation method thereof. The preparation method includes the steps of S1, adding sodium hydroxide into the ethanol solution ofethyl acetohydroxamate, dropwise adding halohydrocarbon, sulfonyl chloride or acyl chloride at the same time to perform substitution reaction, and adding into water to separate out O-substituted ethyl acetohydroxamate; S2, adding the O-substituted ethyl acetohydroxamate into a hydrochloric acid solution, and performing reflux reaction to generate the O-substituted hydroxylamine hydrochloride. Thepreparation method has the advantages that high-purity products can be obtained, and the method is safe, easy in processing, simple in process and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to an O-substituted hydroxylamine hydrochloride and a preparation method thereof. Background technique [0002] O-Alkylhydroxylamine hydrochloride and O-acylhydroxylamine hydrochloride are a class of widely used intermediates in organic synthesis. The main feature is the variability of the substituents on the oxygen, and this type of compound presents diversity. It has special uses in the field of agricultural chemistry, such as plant growth regulators, herbicides and fungicides. It is also used in antidepressant drugs, antiarrhythmic drugs, and antiviral and sedative drugs in human medicine. [0003] At present, the preparation methods of O-alkyl hydroxylamine hydrochloride and O-acyl hydroxylamine hydrochloride compound mainly contain the following methods: [0004] Method 1: N-hydroxyphthalimide reacts with halogenated hydrocarbon or acyl chloride under alkaline cond...

Claims

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Application Information

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IPC IPC(8): C07C239/08C07C303/32C07C309/73C07C239/22
CPCC07C239/08C07C239/22C07C253/30C07C303/28C07C303/32C07C309/73C07C255/64
Inventor 王桂春吕敏杰柳敏
Owner SUZHOU HIGHFINE BIOTECH
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