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Synthesis process of sulfonamide compounds in microwave system

A technology for sulfonamides and synthesis processes, which is applied in the formation/introduction of sulfonyl/sulfinyl groups, the preparation of sulfonic acid amides, and organic chemistry, etc., and can solve problems such as limitations in the use of synthetic schemes, difficulty in obtaining raw materials, and severe reaction conditions. , to achieve the effect of high productivity, environmental friendliness and simple operation

Active Publication Date: 2017-05-10
FUJIAN MEDICAL UNIV
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  • Claims
  • Application Information

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Problems solved by technology

[0003] The synthesis methods of sulfonamide compounds reported in the literature have their own advantages and disadvantages, but there are many steps and complicated procedures, more or less due to the difficulty in obtaining raw materials, the high toxicity of some reagents, the severe reaction conditions and serious environmental pollution, etc. restricted

Method used

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  • Synthesis process of sulfonamide compounds in microwave system
  • Synthesis process of sulfonamide compounds in microwave system
  • Synthesis process of sulfonamide compounds in microwave system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: N-benzylbenzenesulfonamide: 1 mmol of benzenesulfonamide was added to the reaction vessel, followed by adding 2 mmol of ferric chloride, 0.1 mmol of cuprous chloride, 0.01 mmol of potassium carbonate, 4 mL of toluene, and dimethyl Dimethyl formamide (DMF) 3ml. Placed in a microwave reactor and heated to 120 °C under 150 W power for continuous reaction for 30 min. After the reaction was completed, it was cooled to room temperature, concentrated under reduced pressure, and the product was purified by column chromatography to obtain a light yellow solid with a yield of 80%.

Embodiment 2

[0029] Embodiment 2: N-benzyl-4-methylbenzenesulfonamide: add 1 mmol of 4-methylbenzenesulfonamide in the reaction vessel, add ferric chloride 2 mmol, cuprous chloride 0.1mmol, potassium carbonate in sequence 0.01mmol, toluene 4mL, dimethylformamide (DMF) 3ml. Placed in a microwave reactor and heated to 120 °C under 150 W power for continuous reaction for 30 min. After the reaction was completed, it was cooled to room temperature, concentrated under reduced pressure, and the product was purified by column chromatography to obtain a light yellow solid with a yield of 78%.

Embodiment 3

[0030] Example 3: N-benzyl-4-ethylbenzenesulfonamide: add 1 mmol of 4-ethylbenzenesulfonamide to the reaction vessel, add 2 mmol of ferric chloride, 0.1 mmol of cuprous chloride, and potassium carbonate in sequence 0.01mmol, toluene 4mL, dimethylformamide (DMF) 3ml. Placed in a microwave reactor and heated to 120 °C under 150 W power for continuous reaction for 30 min. After the reaction was completed, it was cooled to room temperature, concentrated under reduced pressure, and the product was purified by column chromatography to obtain a light yellow solid with a yield of 76%.

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Abstract

The invention discloses a synthesis process of sulfonamide compounds in a microwave system. The synthesis process is realized by the following steps: by using CuCl as a catalyst and FeCl3 as an oxidant, carrying out carbon-hydrogen activating and carbon-nitrogen coupling reaction in a DMF (Dimethyl Formamide) by substituting sulfanilamide and methylbenzene through microwave heating and efficient catalysis for 10 to 60 minutes; extracting a product by using ethyl acetate; carrying out vacuum concentration; carrying out column chromatographic purification on a product to obtain the sulfonamide compounds. The synthesis process is a method for efficiently preparing the sulfonamide compounds, which is environment-friendly and is simple and convenient to operate. Compared with the prior art, the synthetic process disclosed by the invention has the advantages of remarkably-increased reaction speed compared with that under a conventional heating condition, mild reaction conditions, simple operation, high yield, safety, low cost and environmental protection.

Description

technical field [0001] The invention discloses a method for preparing sulfonamide compounds. That is, using substituted benzenesulfonamides and substituted toluenes as raw materials, introducing microwaves as an auxiliary synthesis method to activate hydrocarbons, has become a method for efficiently catalyzing and rapidly preparing sulfonamide compounds. Background technique [0002] Sulfonamide drugs are artificially synthesized antibacterial drugs, which have been used in clinical practice for nearly 50 years. They are a class of chemotherapeutic drugs used to prevent and treat bacterial infectious diseases. Inhibition, with the advantages of broad antibacterial spectrum and stable properties, has become the first choice for antibacterial drugs in most people's lives. [0003] The synthesis methods of sulfonamide compounds reported in the literature have their own advantages and disadvantages, but there are many steps and complicated procedures, more or less due to the di...

Claims

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Application Information

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IPC IPC(8): C07C303/36C07C311/16C07C311/29C07C311/39C07C311/18C07C311/17C07B45/04
CPCC07B45/04C07C303/36C07C311/16C07C311/29C07C311/39C07C311/18C07C311/17
Inventor 柯方许倩倩刘洋许建华林晨
Owner FUJIAN MEDICAL UNIV
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