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Synthesis method of N-tert-butylbenzenesulfonamide

A technology of tert-butylbenzenesulfonamide and its synthesis method is applied in the fields of sulfonamide preparation and organic chemistry, which can solve the problems of poor reactivity of tert-butyl ether, difficult-to-react raw materials, expensive catalysts, etc., and achieve environmental friendliness, activity and Cheap, the effect of reducing industrial waste

Active Publication Date: 2017-12-12
CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] There are disadvantages such as expensive catalysts and low yields in the prior art. On the basis of the existing work, through a lot of creative work, the inventor aims to develop a kind of benzenesulfonamide as raw material, which generates N-tert-butyl under the action of a catalyst. The industrial production process of phenylbenzenesulfonamide solves the problem of poor reactivity of tert-butyl ether and is difficult to be used as a reaction raw material, and greatly improves the yield of the reaction. It provides a new process for the synthesis of this type of compound and meets the needs of chemical industry , The demand for large-scale production of pharmaceutical industrialization

Method used

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  • Synthesis method of N-tert-butylbenzenesulfonamide

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Experimental program
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Effect test

Embodiment 1

[0018] Add 31.81mmol of benzenesulfonamide, 47.72mmol of tert-butanol, 0.9543mmol of hafnium tetrachloride into a four-necked flask with a thermometer and a reflux condenser, then add 30mL of N-methylpyrrolidone as a solvent, heat to 150°C, and perform HPLC Monitor the reaction (chromatographic conditions: the mobile phase ratio is methanol-water 70:30, the detection wavelength is 254nm), and the disappearance of the raw material benzenesulfonamide is the end of the reaction. The system was cooled to room temperature, the insoluble matter was filtered off, and the filtrate was precipitated under reduced pressure to obtain a yellow liquid, which was the product, with a yield of 97.5%, a purity of 98.8% (HPLC), and MS m / z: 213.08 (M+1,100).

Embodiment 2

[0020] Add 31.81mmol of benzenesulfonamide, 51.36mmol of tert-butyl propionate, and 0.3181mmol of hafnium tetrachloride into a four-neck flask with a thermometer and a reflux condenser, then add 30mL of dimethyl sulfoxide as a solvent, and heat to 139°C. The reaction was monitored by HPLC (chromatographic conditions: the mobile phase ratio was methanol-water 70:30, the detection wavelength was 254nm), and the disappearance of the raw material benzenesulfonamide was the end of the reaction. The system was cooled to room temperature, the insoluble matter was filtered off, and the filtrate was precipitated under reduced pressure to obtain a yellow liquid, which was the product, with a yield of 96.0%, a purity of 98.8% (HPLC), and MS m / z: 213.08 (M+1,100).

Embodiment 3

[0022] Add 31.81mmol of benzenesulfonamide, 43.18mmol of tert-butyl propionate, and 3.181mmol of hafnium tetrachloride into a four-necked flask with a thermometer and a reflux condenser, then add 30mL of xylene as a solvent, heat to 155°C, and monitor by HPLC Reaction (chromatographic conditions: the mobile phase ratio is methanol-water 70:30, the detection wavelength is 254nm), and the disappearance of the raw material benzenesulfonamide is the end of the reaction. The system was cooled to room temperature, the insoluble matter was filtered off, and the filtrate was precipitated under reduced pressure to obtain a yellow liquid, namely the product, with a yield of 95.5%, a purity of 98% (HPLC), and MS m / z: 213.08 (M+1,100).

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Abstract

The invention discloses a synthesis method of N-tert-butylbenzenesulfonamide. The method comprises the following steps: putting benzenesulfonamide, materials, a catalyst and a solvent into a four-necked flask and stirring; heating and carrying out reflowing reaction; when the raw material benzenesulfonamide disappears, reaching a reaction end point to obtain a reactant; cooling the reactant to room temperature; filtering to remove an insoluble substance; carrying out decompression and desolvation to obtain the N-tert-butylbenzenesulfonamide.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of N-tert-butylbenzenesulfonamide. Background technique [0002] Sulfonamide compounds are a class of biologically active substances, which are widely used in pharmaceutical research and development and pesticide development. For example, a class of fungicides, herbicides, insecticides, anticancer drugs and diabetes all contain sulfonamides. Group, wherein the N-tert-butylation reaction of benzenesulfonamide is difficult to carry out due to the steric hindrance effect of tert-butyl group and the electronic effect of sulfonamide group, and the yield is low. Defects and deficiencies of the prior art: Chen Jiayan et al reported in the literature (TiCl4-Mediated Direct N-Alkylation of Sulfonamides with Inactive Ethers", Synlett, 2012, 23, 595-600) that the use of catalyst titanium tetrachloride to catalyze ether compounds A method for preparing N-hydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/40C07C311/16
CPCC07C303/40C07C311/16
Inventor 王凯陈强岳邦毅郝卫强
Owner CHANGZHOU HIGH TECH RES INST OF NANJING UNIV
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