Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • O-substituted hydroxylamine hydrochloride and preparation method thereof
  • O-substituted hydroxylamine hydrochloride and preparation method thereof
  • O-substituted hydroxylamine hydrochloride and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com