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Synthesis method of sulfanilamide compound

A synthetic method and compound technology, applied in the preparation of sulfonamides, organic chemistry, sulfide preparation, etc., can solve the problems of many steps, long reaction routes, and low yields

Active Publication Date: 2021-02-26
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problems of this synthetic route include: long reaction route, many steps, low yield, need to use strong acid in the reaction process, produce unpleasant-smelling organic sulfides, and do not conform to atomic economy, etc.
However, in the above reaction, the scope of application of the sulfonylation reaction substrate of aryl halide is limited to hydrazine compounds, and only specific types of sulfonamide compounds can be synthesized.

Method used

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  • Synthesis method of sulfanilamide compound
  • Synthesis method of sulfanilamide compound
  • Synthesis method of sulfanilamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1. Preparation of compound 5a

[0073]

[0074] In a glove box filled with high-purity argon, DMAP (61.0mg, 2.5equiv), nBuPAD 2 (14.4mg, 20.0mol%), Pd(acac) 2 (7.6mg, 12.5mol%), 4-iodo-1,2-dimethoxybenzene 3a (0.2mmol, 1.0equiv), N-methyl-2-phenylethane-1-amine 4a (0.52mmol ,2.6equiv) add in order figure 1 In tube B equipped with a magnetic stirring bar, add 1ml DMSO at the same time. Quickly weigh compound 1 into tube A equipped with a magnetic stirrer, add 1ml of tetradecane, and then add compound 2 into tube A. Quickly tighten the bottle caps of tubes A and B, then take out the glove box, place the above device on a magnetic stirrer at 95°C and stir for 24 hours. Extract with ethyl ester and water (15ml×3 times), combine the ethyl acetate layers, dry over anhydrous sodium sulfate, concentrate, add 200-300 mesh silica gel and mix to dryness, and obtain the compound 5a shown in formula 1 through column chromatography. Yellow liquid, yield 74%.

[00...

Embodiment 2

[0076] Embodiment 2. Preparation of compound 5b

[0077] The preparation method is the same as that of compound 5a, except that 4-iodo-1,2-dimethoxybenzene is replaced by 1-ethoxy-4-iodobenzene to obtain compound 5b, a white solid, with a yield of 63%.

[0078] Compound 5b: 1 H NMR (400MHz, CDCl 3)δ7.70(d, J=8.8Hz, 2H), 7.34-7.23(m, 3H), 7.21(d, J=6.8Hz, 2H), 6.96(d, J=8.8Hz, 2H), 4.10( q,J=6.8Hz,2H),3.28-3.24(m,2H),2.90-2.86(m,2H),2.76(s,3H),1.46(t,J=6.8Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ162.4, 138.5, 129.6, 129.3, 129.0, 128.7, 126.7, 114.7, 64.1, 52.0, 35.3, 35.0, 14.8; HRMS m / z calculated for C 17 h 21 NO 3 S[M+H] + :320.1315,found:320.1316.

Embodiment 3

[0079] Embodiment 3. Preparation of compound 5c

[0080] The preparation method is the same as that of compound 5a, except that 4-iodo-1,2-dimethoxybenzene is replaced with 1-iodo-4-phenoxybenzene to obtain compound 5c, a yellow liquid, with a yield of 62%.

[0081] Compound 5c: 1 H NMR (400MHz, CDCl 3 )δ7.70(d, J=8.8Hz, 2H), 7.43-7.39(m, 2H), 7.32-7.28(m, 2H), 7.23-7.18(m, 4H), 7.07(d, J=7.6Hz ,2H),7.02(d,J=8.8Hz,2H),3.29-3.25(m,2H),2.89-2.86(m,2H),2.77(s,3H); 13 C NMR (100MHz, CDCl 3 )δ161.6, 155.3, 138.4, 131.6, 130.3, 129.6, 128.9, 128.7, 126.7, 125.0, 120.4, 117.7, 51.9, 35.3, 35.0; HRMS m / z calculated for C 21 h 21 NO 3 S[M+Na] + :390.1134,found:390.1136.

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of sulfonamide compounds. Aiming at the defects of a sulfonamide compound synthesis method in the prior art, the invention adopts the technical scheme that SO2 gas is introduced into a mixture solution of aryl iodide and amine for reaction to obtain the sulfonamide compound. The invention further provides a new SO2 gas generation mode, which is combined with a two-chamber reaction system, wherein the sulfur dioxide gas generated in situ is directly inserted into aryl iodide and amine, and the sulfonamide compound is generated in one step. The synthesis method provided by the invention has following advantages: raw materials are extensive in source and are low-cost and easy-to-prepare; the reaction operation is simple; the substrate universality is high; and economy and practicability is achieved. Therefore, the method has very high practical value and wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of sulfonamide compounds. Background technique [0002] Sulfonamide compounds have extensive and important uses. For example, in the field of medicine, many important drug molecules and active intermediates are sulfa compounds, such as quinolone antibacterial drug enoxacin, tricyclic antidepressant amoxapine, antihistamine desloratadine , intermediates of dopamine D1 agonist fenoldopam, etc. Synthetic sulfonamides have been used clinically as antibacterial drugs for nearly 50 years. They have the advantages of wide antibacterial spectrum, stable properties, easy use, and no food consumption during production. Especially in 1969, after the discovery of the antibacterial synergist—trimethoprim (TMP), combined application with sulfonamides can enhance its antibacterial effect and expand the scope of treatment. Therefore, although a large nu...

Claims

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Application Information

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IPC IPC(8): C07C311/29C07C311/16C07C303/36C07D319/18C07C319/20C07C323/67C07D209/88C07D333/18C07D209/44C07D211/96C07D209/08C07D295/26C07D471/04C07D267/20C07D401/04C07D223/16
CPCC07C303/36C07D319/18C07C319/20C07D209/88C07D333/18C07D209/44C07D211/96C07D209/08C07D295/26C07D471/04C07D267/20C07D401/04C07D223/16C07C311/29C07C311/16C07C323/67
Inventor 练仲贾秀稳
Owner SICHUAN UNIV
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