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Preparation of N-hydroxy diimide

A technology of hydroxyimide and hydroxylamine, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problem of easy decomposition and explosion, unstable hydroxylamine solution, and cannot be promoted and other problems, to achieve the effects of reducing production costs, mild reaction conditions, reaction yield and product purity

Inactive Publication Date: 2009-02-25
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The advantage of this method is that the reaction conditions are relatively mild, and the product purity is higher (more than 98%). The disadvantage is that the hydroxylamine solution is unstable, easily decomposed and exploded; then the cost of producing N-Boc derivatives is extremely high, and it cannot be promoted equally ( Einhorn C, Einhorn J, Marcadal-Abbadi C. Synthetic Communications, 2001, 31(5), 741.)

Method used

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  • Preparation of N-hydroxy diimide
  • Preparation of N-hydroxy diimide
  • Preparation of N-hydroxy diimide

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Add succinic anhydride (1mol), hydroxylamine hydrochloride (1mol), acetic anhydride (0.02mol), trifluoroacetic acid (0.02mol), pyridine (1mol) into a three-necked flask equipped with a stirrer, nitrogen inlet tube, and reflux condenser in sequence. ) and dioxane (400ml). Under the protection of nitrogen, heat up to 100°C, react for 6h, until no succinic anhydride is detected by thin layer chromatography, cool to 60°C, concentrate to dryness under reduced pressure, add 4000ml of ethyl acetate, stir, stand still, pour out the upper clear night , then extracted 4 times with ethyl acetate, each 2000ml, combined ethyl acetate solution, evaporated solvent under reduced pressure, recrystallized with ethyl acetate, decolorized with activated carbon, and obtained white solid, i.e. compound (A), yield 86% , melting point 97 ~ 98 ℃, purity > 99.5%.

Embodiment 2

[0026] Add succinic anhydride (1mol), hydroxylamine hydrochloride (1.05mol), acetic anhydride (0.04mol), trifluoroacetic acid (0.03mol), pyridine ( 1.05mol) and dioxane (400ml). Under the protection of nitrogen, heat up to 100°C, react for 6h, until no succinic anhydride is detected by thin layer chromatography, cool to 60°C, concentrate to dryness under reduced pressure, add 4000ml of ethyl acetate, stir, stand still, pour out the upper clear night , then extracted 4 times with ethyl acetate, each 2000ml, combined ethyl acetate solution, evaporated solvent under reduced pressure, recrystallized with ethyl acetate, activated carbon decolorization, obtained white solid, i.e. compound (A), yield 90% , melting point 97 ~ 98 ℃, purity > 99.5%.

Embodiment 3

[0028] Add maleic anhydride (1mol), hydroxylamine sulfate (1.1mol), acetic anhydride (0.05mol), trifluoroacetic acid (0.05mol), triethyl Amine (1.25mol) and 2-methyltetrahydrofuran (400ml). Under the protection of nitrogen, heat up to 80°C, react for 6h, until there is no maleic anhydride detected by thin layer chromatography, cool to 50°C, concentrate to dryness under reduced pressure, add 4000ml of ethyl acetate, stir, stand still, pour out the upper clear night , extracted 4 times with ethyl acetate, each time 2000ml, combined ethyl acetate solution, evaporated solvent under reduced pressure, then recrystallized with ethyl acetate, activated carbon decolorization, obtained white solid, i.e. compound (B), yield 80% , melting point 148 ~ 149 ℃ (decomposition), purity> 99.5%.

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Abstract

The invention belongs to the technical field of chemical plating auxiliary agent and fine chemical intermediate, and more particularly relates to a method for preparing N-hydroxide radical diimide. The preparation method uses a novel catalyst system which is acetic anhydride / trifluoroacetic acid / organic base, so as to lead the conditions of the reaction for substituting dicarboxylic anhydride and hydroxylamine compound salt to be more mild; the reaction yield coefficient and product purity are improved, thus greatly reducing the production cost and being applicable to mass production and application.

Description

technical field [0001] The invention belongs to the field of electroless plating additives and fine chemical intermediates, and in particular relates to a preparation method of N-hydroxyimide. Background technique [0002] The sodium salt or potassium salt of N-hydroxyimide, as an electroless plating additive, can enhance the stability of the plating solution, improve the brightness of the metal coating, and reduce the content of impurity elements in the coating, thereby greatly improving the metal film. quality. However, as an electroless plating auxiliary, the sodium or potassium salt of N-hydroxyimide is required to have a purity of more than 99%. [0003] N-hydroxyl diimide has been widely used as an intermediate in organic synthesis. ) is an important reagent; N-hydroxysuccinimide is also used to prepare active esters, which inhibit the formation of racemates during peptide coupling, and it can covalently bind to proteins without affecting their biological activity. ...

Claims

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Application Information

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IPC IPC(8): C07D207/46C07D209/50C07D209/66C07D221/06B01J31/04
Inventor 吕银祥
Owner FUDAN UNIV
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