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A kind of preparation method of sulfonamide compound

A compound and sulfonamide technology, which is applied in the field of preparation of sulfonamide compounds, can solve the problems of restricting wide application and achieve the effects of high atom economy, stable process conditions and mild reaction conditions

Active Publication Date: 2019-09-10
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] However, the reactions still require transition metal catalysts, strong corrosive reagents, or relatively dangerous peroxide oxidants, greatly limiting their wide application in the fields of organic synthesis and medicinal chemistry.

Method used

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  • A kind of preparation method of sulfonamide compound
  • A kind of preparation method of sulfonamide compound
  • A kind of preparation method of sulfonamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] At room temperature, p-methylthiophenol (1.24 g, 10 mmol), morpholine (1.75 ml, 20 mmol), acetonitrile (20 mL) and diiodine pentoxide (10 mmol) were successively added into a 50 mL round bottom flask. Then, the reaction mixture was stirred at 60 °C for 12 h (reaction detected by TLC). Then, the reaction was stopped and concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) obtained the corresponding product sulfonamide compound (white solid 1.95 g, yield 81%).

[0035] 1 H NMR (CDCl 3, 500 MHz, ppm): δ 7.66 (d, J = 8.3 Hz, 2H), 7.37 (d, J =8.0 Hz, 2H), 3.76 (t, J = 4.7 Hz, 4H), 3.00 (t, J = 4.8 Hz, 4H), 2.47 (s,3H); C 13 NMR (CDCl 3 , 125MHz, ppm): δ 143.9, 132.1, 129.7, 127.9, 66.1, 46.0, 21.6; HRMS calc. for C 11 h 15 NO 3 SNa (M+Na) + , 264.0670; found, 264.0675.

Embodiment 2

[0037]

[0038] At room temperature, thiophenol (1.03ml, 10mmol), morpholine (1.75ml, 20mmol), acetonitrile (20 mL) and diiodine pentoxide (10 mmol) were successively added into a 50 mL round bottom flask. Then, the reaction mixture was stirred at 60 °C for 12 hours (reaction detected by TLC). Then, the reaction was stopped and concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) obtained the corresponding product sulfonamide compound (yellow solid 1.87g, yield 82%).

[0039] 1 H NMR (CDCl 3 , 500 MHz, ppm): δ 7.77-7.75 (m, 2H), 7.65-7.62 (m, 1H),7.58-7.55 (m, 2H), 3.75 (t, J = 4.7 Hz, 4H), 3.01 (t, J = 4.8 Hz, 4H); 13 C NMR (CDCl 3 , 125 MHz, ppm): δ 135.1, 133.1, 129.1, 127.8, 66.1, 46.0; HRMS calc. for C 10 h 13 NO 3 SNa (M+Na) + , 250.0514; found, 250.0517.

Embodiment 3

[0041]

[0042] At room temperature, p-methoxythiophenol (1.23ml, 10mmol), morpholine (1.75ml, 20mmol), acetonitrile (20 mL) and diiodine pentoxide (10 mmol) were successively added into a 50 mL round bottom flask. Then, the reaction mixture was stirred at 60 °C for 12 hours (reaction detected by TLC). Then, the reaction was stopped and concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) obtained the corresponding product sulfonamide compound (2.20 g of yellow crystals, yield 85%).

[0043] 1 H NMR (CDCl 3 , 500 MHz, ppm): δ 7.70-7.69 (m, 2H), 7.02-7.01 (m, 2H), 3.89 (s, 3H), 3.74 (t, J = 4.7 Hz, 4H), 2.98 (t, J = 4.8 Hz, 4H); 13 C NMR (CDCl 3 , 125 MHz, ppm): δ 163.2, 130.0, 126.7, 114.3, 66.1, 55.7, 46.0; HRMScalc. for C 11 h 15 NO 4 SNa (M+Na) + , 280.0619; found, 280.0622.

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Abstract

The invention discloses a reparation method of a sulfonamides compound. The preparation method includes: using thiophenol and amine which are simple and easy to get as raw materials; enabling the raw materials to be in direct oxidation coupling reaction under mediation of safe and stable iodine pentoxide to prepare sulfonamide. The preparation method has the advantages that reaction conditions are mild (60 DEG C), the raw materials are simple and easy to get and low in price, reaction environment is friendly, a substrate is wide in application range, and metal catalysts and harsh reaction conditions like low or high temperature and zero water and zero oxygen are not needed, so that metal pollution related to common synthesis methods is avoided; the preparation method further has the advantages of simple, convenient and safe operation, stable process condition and easiness in product purification and is suitable for large-scale production.

Description

technical field [0001] The invention belongs to the field of synthetic chemistry, and relates to a preparation method of a sulfonamide compound, in particular to a method for synthesizing a sulfonamide compound by directly utilizing thiophenol and amine oxidative coupling reaction mediated by diiodine pentoxide. Background technique [0002] Sulfonamides are of great significance in practical applications such as chemical research and drug development. Sulfonamide structural fragments not only widely exist in natural products, but also often serve as key structural skeletons of physiologically active molecules and drug molecules. Studies have shown that substances containing this structural fragment have a wide range of biological activities, such as: sterilization, herbicide, insecticide, anticancer, antidiabetic and so on. As shown below, sulfonamide compound A (Sulfamethoxazole or SMZ) is a broad-spectrum antibiotic that has a good inhibitory effect on sensitive bacteria...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/26C07D213/71C07C303/36C07C311/16C07B45/04
Inventor 王桦魏伟朱明慧崔环环王雷雷
Owner QUFU NORMAL UNIV
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