Preparing method of sulfanilamide compound

A technology of aminobenzenesulfonamide and nitrobenzenesulfonamide, which is applied in the field of preparation of p-aminobenzenesulfonamide compounds, can solve problems such as being difficult to store, large and strong acids, and sulfonyl chlorides are toxic, and achieves the effect of a simple method

CN106316938AActive Publication Date: 2017-01-11SOUTH CHINA AGRI UNIV
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
Publication Date
2017-01-11

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Abstract

The invention belongs to the technical field of organic synthesis and the field of sulfonamides, and in particular discloses a preparing method of a sulfanilamide compound. The preparing method particularly comprises the steps of reacting bis (2-nitrophenyl) disulfide and miscellaneous aromatic amine compound under conditions of reducing agent, oxidant and solvent to obtain the sulfanilamide compound. According to the preparing method of a sulfanilamide compound, cheap zirconium salt and copper salt are adopted as catalyst, stable and low toxic disulfide is directly used as sulfonylation reagent, sulfonylation for amine is conducted directly, finishing at usual atmospheric pressure avoids the step of preparing sulfonyl chloride, therefore avoiding using strong corrosive substances as shlorine, thionyl chloride and the like. And the method is more simple and environment-friendly, conforming to the demand of developing green chemical industry in the current world.
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Description

technical field

[0001] The invention belongs to the technical field of organic synthesis and the field of sulfonamide drugs, and specifically relates to a preparation method of p-aminobenzenesulfonamide compound. Background technique

[0002] Sulfonamide compounds are a class of compounds with p-aminobenzenesulfonamide structure, and sulfonamide is a broad-spectrum antibacterial and anti-inflammatory drug, which is used as a chemotherapeutic drug for the prevention and treatment of bacterial infectious diseases. Sulfonamides can inhibit Gram-positive bacteria and some negative bacteria, and can effectively inhibit Streptococcus, Pneumococcus, Salmonella, Corynebacterium pyogenes, Escherichia coli, Staphylococcus, Klebsiella pneumoniae, Pasteurella, Bacillus anthracis, Shigella , Arizona bacteria, etc., are widely used in the prevention and treatment of animal bacterial infection diseases such as livestock, poultry, and animal husbandry.

[0003] At present, the sulfonylatio...

Examples

Embodiment 1

[0032] (1) Synthesis of p-nitrobenzenesulfonamide pyridine:

[0033]

[0034] P-nitrophenyl disulfide (1mmol) and 2-aminopyridine (1.5mmol), in ZrCl 4 (20mol% of 2-aminopyridine) and Cu(OAc) 2 (20mol% of 2-aminopyridine), H 2 o 2 (3 mmol) in acetonitrile (4 mL) solvent, the reaction was stirred at 60° C. for 4 hours. Cool after the reaction, the mixture is diluted with AcOEt, washed with water, extracted, the organic phase is dried and filtered with suction, the filtrate is rotary evaporated, the residue is chromatographed, rinsed with an organic solvent, detected by TLC, the effluents containing the product are combined and rotary evaporated, vacuum After drying, p-nitrobenzenesulfonamide pyridine was obtained with a yield of 83%.

[0035] In the above step (1), the target product can also be obtained by using other catalysts. When other conditions remain unchanged, the catalyst is replaced by Cu(OAc) 2 When, the productive rate of target product p-nitrobenzenesulfona...