Process for producing 4-ethynyl benzene sulfonamide (I)

A technology of ethynylbenzenesulfonamide and chlorosulfonylphenyl, which is applied in the field of preparation of 4-ethynylbenzenesulfonamide, can solve the problems of two kinds of raw materials and metal catalysts being expensive and restricting large-scale production, and achieves simple and convenient operation, Reduction of purification steps and easy availability of raw materials

Inactive Publication Date: 2011-11-16
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The two raw materials and metal catalysts used in this method are very expensive, and the metal-catalyzed reaction requires strict anhydrous and oxygen-free operating conditions, which limits its large-scale production

Method used

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  • Process for producing 4-ethynyl benzene sulfonamide (I)
  • Process for producing 4-ethynyl benzene sulfonamide (I)
  • Process for producing 4-ethynyl benzene sulfonamide (I)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Preparation of trans-4-chlorosulfonyl cinnamic acid (II)

[0031] resolve resolution:

[0032]

[0033] Chlorosulfonic acid (60 mL, 0.9 mol) was placed in a 250 mL round bottom flask and cooled to 0 °C with an ice bath. Cinnamic acid (14.8 g, 0.1 mol) was added to the flask in 8 portions over 1.5 hours. Control the reaction temperature at 0°C for 18 hours. The ice bath was removed, and the reaction solution naturally returned to room temperature. After heating to 60° C. for 0.8 hours, the oil bath was removed again, and the reaction solution was naturally cooled to room temperature. The resulting brown-red reaction solution was slowly poured into 600 mL of ice water. Let stand, filter, wash the filter cake with ice water, recrystallize in 300mL glacial acetic acid, filter, and the filtrate is a white solid. P 2 o 5 After drying, white trans-4-chlorosulfonyl cinnamic acid (II) is obtained. Wherein, the molar ratio of chlorosulfonic acid and cinnamic acid is...

Embodiment 2

[0042] (1) Preparation of trans-4-chlorosulfonyl cinnamic acid (II)

[0043] Chlorosulfonic acid (80 mL, 1.2 mol) was placed in a 250 mL round bottom flask and cooled to 0 °C with an ice bath. Cinnamic acid (14.8 g, 0.1 mol) was added to the flask in 10 portions over 2.5 hours. Control the reaction temperature at 0°C for 16 hours. The ice bath was removed, and the reaction solution naturally returned to room temperature. After being heated to 55° C. for 1.2 hours, the oil bath was removed again, and the reaction solution was naturally cooled to room temperature. The resulting brown-red reaction solution was slowly poured into 600 mL of ice water. Let stand, filter, wash the filter cake with ice water, recrystallize in 300mL glacial acetic acid, filter, and the filtrate is a white solid. P 2 o 5 After drying, white trans-4-chlorosulfonyl cinnamic acid was obtained. Wherein, the molar ratio of chlorosulfonic acid and cinnamic acid is 12:1.

[0044] (2) Preparation of 3-(4...

Embodiment 3

[0051] (1) Preparation of trans-4-chlorosulfonyl cinnamic acid (II)

[0052] Chlorosulfonic acid (60 mL, 0.9 mol) was placed in a 250 mL round bottom flask and cooled to 0 °C with an ice bath. Cinnamic acid (14.8 g, 0.1 mol) was added to the flask in 8 portions over 1.5 hours. Control the reaction temperature at 0°C for 18 hours. The ice bath was removed, and the reaction solution naturally returned to room temperature. After heating to 60° C. for 0.8 hours, the oil bath was removed again, and the reaction solution was naturally cooled to room temperature. The resulting brown-red reaction solution was slowly poured into 600 mL of ice water. Let stand, filter, wash the filter cake with ice water, recrystallize in 300mL glacial acetic acid, filter, and the filtrate is a white solid. P 2 o 5 After drying, white trans-4-chlorosulfonyl cinnamic acid was obtained. Wherein, the molar ratio of chlorosulfonic acid and cinnamic acid is 9:1.

[0053] (2) Preparation of 3-(4-chloro...

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Abstract

The invention belongs to the synthesis technical field of pharmaceutical intermediates, in particular to a preparation method of 4-ethynyl benzene sulfonamide (I). The preparation method takes anti-4-chlorosulfonyl cinnamon acid as raw material and firstly carries out addition reaction with the liquid bromine in acetic acid to generate 3-(4-chlorosulfonyl phenyl)-2 and 3-dibromo propionate acid; the 3-dibromo propionate acid takes N and N-dimethylformamide as a solvent and is added with ammonia or aliphatic amine or the mixture of aromatic amine and triethylamine to carry out microwave reaction for 0.5 to 1 minute and the intermediate, 4-(2-bromine ethylene) benzene sulfonamide, can be synthesized by the two-step reaction of sulfonamidation and decarboxylation; the 4-ethynyl benzene sulfonamide is synthesized by means of a one-pot method after sodium ethoxide is added directly into a reaction system and the reaction occurs at the temperature of 60 to 80 DEG C without separating the intermediate. The 4-ethynyl benzene sulfonamide synthesized by the method has very important application prospects in the fields such as biomedicine and medicine, etc.; the compound comprises the sulphonylamino and terminal alkynyl and is a valuable synthesized 'building block' in organic chemistry, more particularly, the compound replaces phenylacetylene to be widely used in aromatic heterocycles such as triazole, etc.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of 4-ethynylbenzenesulfonamide (I). Background technique [0002] The 4-ethynylbenzenesulfonamide synthesized by this method has two important functional groups of sulfonamide group and terminal alkynyl group at the same time, so it has great potential in fields such as organic chemistry, macromolecular materials, biomedicine, medicine and pesticide intermediates. Very important application prospect. This type of compound contains a sulfonamide group, which is firstly the parent of very important sulfonamide drugs; this type of compound contains a terminal alkynyl group, which is a valuable synthetic "building block" in organic chemistry. In particular, substituted phenylacetylene is an important electronic chemical raw material. It has shown excellent characteristics in new liquid crystal materials, special catalysts, elect...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/15C07C303/36
Inventor 匡春香张文生赵国华
Owner TONGJI UNIV
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