Method for synthesizing benzene sulfonamide compounds

A technology of benzenesulfonamide and compound, which is applied in the preparation of sulfonic acid amide, chemical instruments and methods, organic compound/hydride/coordination complex catalyst, etc. The problem of poor reactivity of base ethers, etc., achieves broad-scale industrial application prospects and market potential, high-efficiency reaction, and mild reaction effects.

Inactive Publication Date: 2014-05-28
甘肃皓骏药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction yield is generally very low and it is difficult to realize large-scale industrial production, and there is no market prospect
[0013] As we all know, tertiary hydrocarbyl alcohols or ether reactions are prone to elimination reactions to obtain olefins and cannot effectively prepare N-tertiary hydrocarbyl substituted amides. This is mainly because the steric hindrance of the amide aminating agent makes the intermediate tertiary carbocation easier to carry out Elimination reactions, combined with complex and less predictable catalytic systems, make it difficult to select a suitable catalytic system
[0014] Based on the disadvantages of insufficient material sources and generally low yields in the above-mentioned prior art, as well as the difficulty in the research and development of the catalytic system, the inventors, through a lot of creative work, aimed to develop a kind of tert-butyl ether The industrial catalytic method for preparing N-tert-butyl substituted benzenesulfonamide as raw material solves the problem that tert-butyl ether has poor reactivity and is difficult to be used as a reaction raw material, and greatly improves the yield of the reaction, providing a source for the synthesis of such compounds A brand-new process that meets the needs of chemical industry, pharmaceutical production and technological development, and realizes the goal of initial large-scale production of N-tert-butylamide

Method used

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  • Method for synthesizing benzene sulfonamide compounds
  • Method for synthesizing benzene sulfonamide compounds
  • Method for synthesizing benzene sulfonamide compounds

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0037] Weigh the mixture of ethyltriphenylphosphonium bromide, AgCl and porphyrin according to the mass ratio of 0.7:1.2:1, grind and mix evenly to obtain the catalyst of the present invention, which is used in the following specific examples according to the dosage.

Embodiment 1

[0039]

[0040] Add 300ml of toluene to the reactor, then add 1mol of methyl tert-butyl ether and 1.5mol of benzenesulfonamide, heat up to 60°C, then add 0.3g of catalyst, and stir the reaction for 8 hours under the thermometer. After the reaction, N-tert-butylbenzenesulfonamide was obtained by vacuum concentration, column chromatography separation and drying, with a yield of 96.3% and a purity of 98.2% (HPLC).

[0041] 1 H-NMR (CDCl 3 , 270MHz) δ: 7.92 (m, 2H), 7.49, (m, 3H), 4.82 (br, 1H), 1.21 (s, 9H).

[0042] MS m / z: 213.08 (M+1,100).

Embodiment 2

[0044]

[0045] Add 300ml of toluene to the reactor, then add 1mol of methyl tert-butyl ether and 1.4mol of p-toluenesulfonamide, heat up to 50°C, then add 0.5g of catalyst to it and stir for 7 hours. Chromatographic separation and drying gave N-tert-butyl p-toluenesulfonamide with a yield of 96.5% and a purity of 98.4% (HPLC).

[0046] 1 H-NMR (CDCl 3 ,270MHz) δ: 7.78(d,2H), 7.29(d,2H), 4.85(br,1H), 2.44(s,3H), 1.22(s,9H).

[0047] MS m / z: 227.06 (M+1,100).

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Abstract

The invention relates to a method for preparing benzene sulfonamide compounds. In the method, a ternary catalyzing system of ethyltriphenylphosphonium bromide-silver compounds-porphyrin is adopted; the method for preparing N-tert-Butylbenzenesulfenamide from the reaction of methyl tertiary butyl ether with a weak reactivity and benzene sulfonamide compounds is realized; remarkably technical effects of preferable reaction temperature, high yield and good universality are achieved; moreover, as appropriate additives are added in the reaction, the collision between molecules is promoted and the reaction time is shortened; the method has favorable industrialization perspective and industrialized production value.

Description

technical field [0001] The present invention relates to the synthetic method of N-hydrocarbylbenzenesulfonamide compound in the field of organic synthesis, more specifically relate to a kind of by asymmetric tert-butyl ether and aminating agent The invention relates to an industrial method for synthesizing N-tert-butyl substituted benzenesulfonamide compounds by reacting under the action of a three-way catalytic system of morphine, which belongs to the field of organic chemical intermediates. Background technique [0002] As a very important pharmaceutical intermediate, sulfonamide compounds have been widely used in biomedicine, organic synthesis and other fields, especially in the preparation of organic amine chemical raw materials and the research and development of new drugs. The field of production, and the sulfonamide structure as a medicinal component also commonly exists in traditional medicines. [0003] There have been many reports on the synthetic method of N-hydr...

Claims

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Application Information

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IPC IPC(8): C07C303/36C07C311/16C07C311/27B01J31/26
Inventor 杨雪飞
Owner 甘肃皓骏药业有限公司
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