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Preparation method for p-carboxybenzene sulfonamide

A technology of carboxybenzenesulfonamide and methyl, which is applied in the field of organic synthesis, can solve the problems of high pollution and achieve the effect of avoiding pollution

Active Publication Date: 2016-06-22
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to overcome the existing high-pollution defect in the method for preparing p-carboxybenzenesulfonamide, and provide a new preparation method of p-carboxybenzenesulfonamide

Method used

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  • Preparation method for p-carboxybenzene sulfonamide
  • Preparation method for p-carboxybenzene sulfonamide
  • Preparation method for p-carboxybenzene sulfonamide

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preparation example Construction

[0018] The invention provides a kind of preparation method of p-carboxybenzenesulfonamide, the method comprises: in the presence of alkali metal halide salt, the compound of structure shown in formula (1), alkali metal halide salt and protonic acid are carried out in water Contact, the alkali metal halide is selected from LiBrO 3 , KBrO 3 and NaBrO 3 One or more of, the alkali metal halide salt is one or more selected from LiBr, KBr and NaBr,

[0019]

[0020] In formula (1), R is a C1-C3 linear or branched alkyl group.

[0021] In the present invention, examples of the C1-C3 linear or branched alkyl group may include, but not limited to: methyl, ethyl, n-propyl or isopropyl. According to the method of the present invention, only one compound having the structure represented by formula (1) may be used, or two or more compounds having the structure represented by formula (1) may be used in combination. When two or more compounds having structures represented by formula (...

Embodiment approach

[0036] According to a preferred embodiment of the present invention, the preparation method of the p-carboxybenzenesulfonamide comprises: in the presence of an alkali metal halide salt, under stirring, the compound of the structure shown in formula (1), an alkali metal halide The acid salt and alkali metal halide salt are dissolved in water, and the protonic acid is added dropwise to the obtained aqueous solution in the form of a solution.

[0037] According to the method of the present invention, in order to obtain a product with higher purity, preferably, the method further includes purifying the contacted product. The step of purifying is preferably by washing the product with a solvent, preferably water.

[0038] The present invention will be described in detail below by way of examples.

[0039] In the following examples and comparative examples, p-toluenesulfonamide was commercially purchased from Beijing Coupling Technology Co., Ltd. Except that, unless otherwise speci...

Embodiment 1

[0045] This embodiment is used to illustrate the preparation method of p-carboxybenzenesulfonamide provided by the invention.

[0046] At room temperature (25°C), put 17.1g (100mmol) of p-toluenesulfonamide, 16.6g (110mmol) of sodium bromate, and 0.1g (1mmol) of sodium bromide into a 500mL four-neck flask, and add 150mL of water as a solvent , start the stirring device, open the condensed water, be warming up to 95 ℃, after the above-mentioned solid dissolves completely (dissolution time is 30min), in the reaction solution, dropwise (drop speed is 0.6mL / min) concentration is the concentrated hydrochloric acid of 37% by weight 7g (71mmol), the color of the reaction solution gradually turns red, keep warm at 100°C, solid appears after about 1h, then react with stirring for 12h, turn off the heating until the color of the reaction solution fades completely, cool the reaction solution to room temperature and then Suction filtration, washing with water and drying were carried out t...

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Abstract

The invention relates to the field of organic synthesis, and discloses a preparation method for p-carboxybenzene sulfonamide. The method comprises the following step: making a compound shown as a formula (1), alkali metal halate and protonic acid contact one another in water in the presence of alkali metal halide salt, wherein the alkali metal halate is selected from one or more of LiBrO3, KBrO3 and NaBrO3; the alkali metal halide salt is selected from one or more of LiBr, KBr and NaBr. The method has the advantages of simple steps and environmental friendliness, and pollution caused by use of a heavy metal oxidant is avoided.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for preparing p-carboxybenzenesulfonamide. Background technique [0002] p-Carboxylbenzenesulfonamide (Carzenide), also known as 4-sulfamoylbenzoic acid, 4-sulfamoylbenzoic acid or p-sulfonamidebenzoic acid, the molecular structure is as follows: [0003] [0004] p-Carboxybenzenesulfonamide is an important intermediate in organic synthesis, used in the synthesis of fine chemical products such as medicine, for example, in the pharmaceutical industry for the synthesis of probenecid and harazone. [0005] Oxidation reaction is an important class of organic unit reactions, and at the same time, oxidation process is also one of the factors leading to environmental pollution. At present, the synthesis of p-carboxybenzenesulfonamide is mainly obtained through the oxidation reaction of p-toluenesulfonamide and potassium permanganate or potassium dichromate. However, these ...

Claims

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Application Information

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IPC IPC(8): C07C311/16C07C303/40
CPCC07C303/40C07C311/16
Inventor 王宝乾孙自培焦体李辛夷
Owner NUTRICHEM LAB CO LTD
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