Method of preparing sulfone amide and method of using said sulfone smine to prepare N-substituted imine

A technology for amide sulfone and sulfinate, which is applied in the field of preparing amide sulfone and preparing N-substituted imine by using the amide sulfone, can solve the problems of being unsuitable for large-scale preparation, having no versatility, unfavorable production and application, etc., and achieving The effect of avoiding excessive waste acid production, reducing post-processing burden, and being easy to separate and purify

Inactive Publication Date: 2008-10-01
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, these methods are limited to the research purpose of the laboratory, using the direct condensation of aldehyde and amide, the conditions are harsh, not suitable for large-scale preparation, not universal, and more difficult to put into industrial production
The method for preparing amide sulfone by condensation reaction in the above-mentioned published documents has an excess of dozens of times of acid, and the reaction conditions are severe, which needs to be improved, especially the environmental hazard caused by a large amount of waste acid during the preparation of amide sulfone, which is not conducive to the production and application of the disclosed method.

Method used

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  • Method of preparing sulfone amide and method of using said sulfone smine to prepare N-substituted imine

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Experimental program
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Embodiment 1

[0040] Embodiment 1: preparation amide sulfone (Ia)

[0041] Benzaldehyde (1.0 ml, 10mmol), benzenesulfonamide (3.2 grams, 20mmol), ammonium p-toluenesulfinate (2.7 grams, 15mmol), sulfamic acid (1.9 grams, 20mmol) were dissolved in water-ethanol mixed solvent (vol. ratio 1:2, 40 ml), stirred at 40°C for 6 hours. The precipitate was washed with water (2×15 ml) and petroleum ether (15 ml) to obtain 3.2 g of product (Ia).

Embodiment 2

[0042] Embodiment 2: preparation amide sulfone (Ib)

[0043] n-valeraldehyde (2.4ml, 25mmol), p-toluenesulfinamide (6.2g, 40mmol), sodium p-toluenesulfinate (8.9g, 50mmol), sulfamic acid (5.8g, 60mmol) were dissolved in water-ethanol mixture Solvent (volume ratio 1:1, 100 ml), stirred at 0°C for 12 hours. The precipitate was washed with water (2×40 ml) and petroleum ether (40 ml) to obtain 8.5 g of product (Ib).

Embodiment 3

[0044] Embodiment 3: Preparation of amide sulfone (Ic)

[0045] Crotonal (3.9ml, 50mmol), phenoxyphosphonamide (15g, 60mmol), ammonium p-toluenesulfinate (8.7g, 50mmol), sulfamic acid (7.7g, 80mmol) were dissolved in water-ethanol mixed solvent (volume ratio 1:2, 200 ml), stirred at 20°C for 12 hours. The precipitate was washed with water (2×60 ml) and petroleum ether (60 ml) to obtain 21 g of product (Ic).

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Abstract

The present invention discloses a method for preparing amidosulfone and preparing N-substituted imine by using said amidosulfone. The method for preparing amidosulfone is characterized by that in water or mixed solution of water and organic solvent said method utilizes the action of protonic acid to make aldehyde, acylamide and sulfinate undergo the process of condensation reaction so as to form the amidosulfone, and the method for preparing N-substitute imine includes the following steps: adopting the above-mentioned amidosulfone and making it be reacted in the double-phase medium formed from organic phase and alkali-containing water phase, using alkali to remove sulfinic acid from amidosulfone to form N-substituted imine, separating organic phase to obtain said product and separating water phase to recover sulfinate.

Description

technical field [0001] The invention relates to a method for preparing amide sulfone and using the amide sulfone to prepare N-substituted imine. Background technique [0002] Amide sulfone is a variety of fine chemical intermediates, components of pharmaceutical actives, especially raw materials for the preparation of N-substituted imines. The method for preparing amide sulfone by condensation reaction was first reported by J.Strating's group (J.B.Engberts and J.Strating, Recl.Trav.Chim.Pays-B., 1965,84,942-950; H.Meijer, R.M.Tel, J.Strating and J.B.Engberts, Recl.Trav.Chim.Pays-B., 1973, 92, 72-82.), this work and the similar work after that, all adopt formic acid or acetic acid as solvent and do acid simultaneously, and the shortcoming is acid If the excess is more than 30 to 100 times (mole), the waste acid after the reaction will cause pollution and the post-treatment will be difficult. [0003] N-substituted imines are widely used in industrial production as pharmaceu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/36C07C311/00C07F9/28
Inventor 李振江任星华万红贵韦萍石玉瑚欧阳平凯
Owner NANJING TECH UNIV
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