次氯酸钠水溶液氧化二硫醚制备磺酰氯Synthesis of sulfonyl chloride from disulfides using sodium hypochlorite solution
王靖文,黄晓程,李璐婷,姚志湘,粟晖,李彦青
摘要(Abstract):
本研究以芳基二硫醚为原料,在乙酸溶剂中,使用质量分数为10%的次氯酸钠(NaClO)水溶液作为氧化剂,合成芳基磺酰氯;以二苯基二硫醚为模型底物,系统考察了溶剂种类、反应温度和NaClO水溶液用量(物质的量)对目标产物产率的影响,从而确定最佳反应条件:质量分数为10%的NaClO水溶液与芳基二硫醚的物质的量比为5:1,以乙酸为溶剂,在反应温度为15℃条件下反应1 min,可获得产率为52%~75%的相应芳基磺酰氯产物。所有产物结构均经氢-1核磁共振波谱法(~1H NMR)、碳-13核磁共振波谱法(~(13)C NMR)及气相色谱-质谱法(GC-MS)表征确证。本方法具有反应速度快、操作简便、底物适用范围广等优点,为从二硫醚中制备磺酰氯提供了一条便捷、高效的合成路径。
关键词(KeyWords): 次氯酸钠;乙酸;磺酰氯;二硫醚;氧化氯化
基金项目(Foundation): 广西科技大学博士基金项目(校科博14Z05);; 广西科技计划项目(2022AC21032)资助
作者(Author): 王靖文,黄晓程,李璐婷,姚志湘,粟晖,李彦青
DOI: 10.16375/j.cnki.cn45-1395/t.2026.03.015
参考文献(References):
- [1]DEVADOSS T. Synthetic applications of p-toluenesulfonyl chloride:a recent update[J]. Journal of Molecular Structure,2023,1289:135850.
- [2]AHJEL S W,HASSAN S M,HUSSEIN S F. Antineoplastic effect of new synthesized compounds of 2-thiouracil sulfonamide derivatives against ovarian and breast carcinoma cells“In vitro study”[J]. Systematic Reviews in Pharmacy,2020,229-237.
- [3]CHENG Y D,HWANG T L,WANG H H,et al. Anthranilic acid-based inhibitors of phosphodiesterase:design,synthesis,and bioactive evaluation[J]. Organic&Biomolecular Chemistry,2011,9(20):7113-7125.
- [4]HOFMANN D,GANS E,KR??LL J,et al. Sustainable synthesis of balsalazide and sulfasalazine based on diazotization with low concentrations of nitrogen dioxide in air[J].Chemistry–A European Journal,2017,23(17):4042-4045.
- [5]SAXENA N,SRIVASTAV N,KUMAR A,et al. Adoption of green methodology in industry for the synthesis of Sildenafil citrate and Celecoxib:a case study[J]. Materials Today:Proceedings,2022,60:1021-1025.
- [6]张亮亮,郭长彬,郑晓霖,等.磺酰氯合成方法研究进展[J].合成化学,2009,17(2):133-139.
- [7]张蕊.苯磺酰氯类化合物的几种合成方法[J].广东化工,2020,47(1):100,84.
- [8]虞巡冬.对乙酰氨基苯磺酰氯合成工艺研究[D].北京:北京化工大学,2022.
- [9]HOLDREGE C T,BABEL R B,CHENEY L C. Synthesis of trifluoromethylated compounds possessing diuretic activity1[J]. Journal of the American Chemical Society,1959,81(18):4807-4810.
- [10]WATSON R J,BATTY D,BAXTER A D,et al. An enantioselective synthesis of sulphonamide hydroxamic acids as matrix metalloproteinase inhibitors[J]. Tetrahedron Letters,2002,43(4):683-685.
- [11]SURYA PRAKASH G K,MATHEW T,PANJA C,et al.Chlorotrimethylsilane-nitrate salts as oxidants:direct oxidative conversion of thiols and disulfides to sulfonyl chlorides[J]. The Journal of Organic Chemistry,2007,72(15):5847-5850.
- [12]HUANG Y H,BENNETT F,VERMA V,et al. A notable conversion of a thiolacetate to its corresponding sulfonyl chloride[J]. Tetrahedron Letters,2012,53(26):3203-3205.
- [13]BAHRAMI K,KHODAEI M,SOHEILIZAD M. A novel,practical synthesis of sulfonyl chlorides from thiol and disulfide derivatives[J]. Synlett,2009,2009(17):2773-2776.
- [14]JEREB M , HRIBERNIK L. Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions[J].Green Chemistry,2017,19(9):2286-2295.
- [15]PARNIAN R,SOLEIMANI D E,BAHRAMI P K. A practical method for the preparation of sulfonyl chlorides and sulfonamides from thiols using H2O2-TAPC reagent system[J]. ChemistrySelect,2019,4(29):8554-8557.
- [16]MADABHUSHI S,JILLELLA R,SRIRAMOJU V,et al.Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX(X=Cl or Br)in water[J]. Green Chemistry,2014,16(6):3125-3131.
- [17]SILVA-CUEVAS C,PEREZ-ARRIETA C,POLINDARAGARC??A L A,et al. Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS-iPrOH[J]. Tetrahedron Letters,2017,58(23):2244-2247.
- [18]KIRIHARA M,KIMURA Y,YAMAHARA S,et al.Synthesis of sulfonyl halides from disulfides or thiols using sodium hypochlorite pentahydrate(NaOCl·5H2O)crystals[J].Synthesis,2022,54(18):4120-4128.
- [19]REZA MASSAH A,SAYADI S,EBRAHIMI S. A green,mild and efficient one-pot method for the synthesis of sulfonamides from thiols and disulfides in water[J]. RSC Advances,2012,2(16):6606-6616.
- [20]JOYARD Y,PAPAMICA??L C,BOHN P,et al. Synthesis of sulfonic acid derivatives by oxidative deprotection of thiols using tert-butyl hypochlorite[J]. Organic Letters,2013,15(9):2294-2297.
- [21]OKADA T,MATSUMURO H,IWAI T,et al. An efficient method for the preparation of sulfonyl chlorides:reaction of disulfides or thiols with sodium hypochlorite pentahydrate(NaOCl·5H2O)crystals[J]. Chemistry Letters,2015,44(2):185-187.
- [22]GAYAKWAD E M,PATIL V V,SHANKARLING G S.Nonanebis(peroxoic acid)mediated efficient and selective oxidation of sulfide[J]. New Journal of Chemistry,2016,40(1):223-230.
- [23]LIU K J,DENG J H,YANG J,et al. Selective oxidation of(hetero)sulfides with molecular oxygen under clean conditions[J]. Green Chemistry,2020,22(2):433-438.
- [24]GAYAKWAD E M,PATIL V V,SHANKARLING G S.Nonanebis(peroxoic acid)mediated efficient and selective oxidation of sulfide[J]. New Journal of Chemistry,2016,40(1):223-230.
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