Synthesis of N-acetyl-4-methyl-benzenesulfonamide from Chloramine-T

Yıl 2020, Cilt: 10 Sayı: 2, 117 - 124, 31.12.2020

Latif Kelebekli

Öz

The synthesis of N-acetyl-4-methyl-benzenesulfonamide is reported. Reaction of N-chloro-p-toluenesulfonamide by acetyl chloride (AcCl) in the presence or absence of OsO4 gave the desired compound. The synthesized compound was characterized by FT-IR, 1H-NMR, 13C-NMR and HRMS analyses.
Bu çalışmada, N-asetil-4-metil-benzensülfonamidin sentezi rapor edildi. N-kloro-p-toluensülfonamidin OsO4 varlığında veya yokluğunda asetil klorür (AcCl) ile reaksiyonu beklenen bileşiği verdi. Sentezlenen bileşik FT-IR, 1H-NMR, 13C-NMR ve HRMS analizleri ile karakterize edildi.

Anahtar Kelimeler

N-acylsulfonamide, N-acylation, chloramine-T, acetyl chloride

Kaynakça

• 1. Banwell M G, Crasto C F, Easton C J, Forrest A K, Karoli T, March D R, Mensah L, Nairn M R, O'Hanlon P J, Oldham M D & Yue W (2000). Analogues of SB-203207 as Inhibitors of tRNA Synthetases. Bioorganic & Medicinal Chemistry Letters 10: 2263–2266.
• 2. Bentley T W, Llewellyn G & McAlister J A (1996). SN2 Mechanism for Alcoholysis, Aminolysis, and Hydrolysis of Acetyl Chloride. Journal of Organic Chemistry 61: 7927-7932.
• 3. Berredjem M, Bouchareb F, Kaki S A, Dekhil M & Aouf N E (2017). Synthesis and antibacterial activity of novel N-acylsulfonamides. Arabian Journal of Chemistry 10: S1095–S1099.
• 4. Bishop E & Jennings V J (1958). Titrimetric analysis with chloramine- T-I. The status of chloramine-T as a titrimetric reagent. Talanta 1: 197–212.
• 5. Chang L L, Ashton W T, Flanagan K L, Chen T B, O'Malley S S, Zingaro G J, Siegl P K S, Kivlighn S D, Lotti V J, Chang R S L & Greenlee W J (1994). Triazolinone Biphenylsulfonamides as Angiotensin II Receptor Antagonists with High Affinity for Both the AT1 and AT2 Subtypes. Journal of Medicinal Chemistry 37: 4464–4478.
• 6. Fu S, Lian X, Ma T, Chen W, Zheng M & Zeng W (2010). TiCl4-promoted direct N-acylation of sulfonamide with carboxylic ester. Tetrahedron Letters 51: 5834–5837.
• 7. Geetanjali A (2005). Chloramine-T (Sodium N-Chloro-ptoluenesulfonamide). Synlett 18: 2857–2858.
• 8. Ghasemi M H, Kowsari E & Hosseini S K (2016). Catalytic activity of magnetic Fe3O4@Diatomite earth and acetic acid for the N-acylation of sulfonamides. Tetrahedron Letters 57: 387–391.
• 9. Hardy F F & Johnston J P (1973). The interactions of Nbromo- N-sodiumbenzenesulfonamide (bromamine-B) with pnitrophenoxide ion. Journal of the Chemical Society, Perkin Transactions, vol. 2, 742–750.
• 10. Hasegawa T & Yamamoto H (2000). A Practical Synthesis of Optically Active (R)-2- Propyloctanoic Acid: Therapeutic Agent for Alzheimer's Disease. Bulletin of the Chemical Society of Japan 73: 423–428.
• 11. Heidler P & Link A (2005). N-acyl-N-alkyl-sulfonamide anchors derived from Kenner's safety-catch linker: powerful tools in bioorganic and medicinal chemistry. Bioorganic & Medicinal Chemistry 13: 585–599.
• 12. Ishizuka N, Matsumura K, Hayashi K, Sakai K & Yamamori T (2000). An Efficient Method for the Preparation of Enantiomerically Pure N-Acylarylsulfonamides Having an Asymmetric Center at the α-Position: Condensation of Acid Chlorides and Arylsulfonamides Under Solid-Liquid Two-Phase Conditions. Synthesis 6: 784–788.
• 13. Jagadeesh R V & Puttaswamy P (2008). Ru(III), Os(VIII), Pd(II) and Pt(IV) catalysed oxidation of glycyl-glycine by sodium Nchloro- p-toluenesulfonamide: comparative mechanistic aspects and kinetic modelling. Journal of Physical Organic Chemistry 21: 844–858.
• 14. Johnson D C & Widlanski T S (2001). Facile synthesis of 5-(N-acyl sulfonamide) derivatized Nucleosides. Tetrahedron Letters 42: 3677–3679.
• 15. Karanfil A, Şahin E & Kelebekli L (2020). Synthesis of novel tetrols from syn-bisepoxide: Preparation of halogenated bicyclo[4.2.0] inositols. Tetrahedron 76: 131000.
• 16. Kelebekli L & Atlı I (2019). Stereoselective synthesis of a new methyl-substituted inositol Derivative. Tetrahedron 75: 130531.
• 17. Kelebekli L, Aksu K & Şahin E (2018). Regio- and stereospecific synthesis of DL-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol. Tetrahedron Letters 59: 1258–1260.
• 18. Kelebekli L, Balcı N & Şahin E (2014). Stereospecific synthesis of highly substituted novel carbasugar as carbonic anhydrase inhibitors: decahydronaphthalene-1,2,3,4,5,6,7-heptol. Tetrahedron 70: 5175–5181.
• 19. Kelebekli L (2007). Stereospecific synthesis of 1,4-di-O-methyl-myo-inositol (Liriodendritol). Journal of Chemical Research 11: 626–628.
• 20. Kelebekli L (2013). Stereoselective synthesis of tricyclo[6.2.2.02,7]dodecane-3,6,9,10-tetrol via selective reduction of α,β-unsaturated 1,4-diketone. Synthetic Communications 43: 2998–3009.
• 21. Kolvari E, Ghorbani-Choghamarani A, Salehi P, Shirini F & Zolfigol M A (2007). Application of N-Halo Reagents in Organic Synthesis. Journal of the Iranian Chemistry Society 4: 126–174.
• 22. Kondo K, Sekimoto E, Nakao J & Murakami Y (2000). Studies on Development of Sufficiently Chemoselective N-Acylation Reagents: N-Acyl-N-(2,3,4,5,6-pentafuorophenyl) methanesulfonamides. Tetrahedron 56: 5843–5856.
• 23. Kondo K, Sekimoto E, Miki K & Murakami Y (1998). A versatile synthon for chemoselective N-acylation reagents, 2-fluoro-N-mesylaniline. Journal of the Chemical Society, Perkin Transactions 1. 2973–2974.
• 24. Martin M T, Roschangar F & Eaddy J F (2003). Practical acid-catalyzed acylation of sulfonamides with carboxylic acid anhydrides. Tetrahedron Letters 44: 5461–5463.
• 25. Massah A R, Dabagh M, Afshar M, Momeni A R, Aliyan H & Naghash H J (2007). A Convenient and Efficient Synthesis of N-Acylsulfonamides in the Presence of Silica Phosphoric Acid under Heterogeneous and Solvent-Free Conditions. Turkish Journal of Chemistry 31: 611–616.
• 26. Massah A R, Dabagh M, Shahidi S, Naghash H J, Momeni A R & Aliyan H (2009). P2O5/SiO2 as an Efficient and Recyclable Catalyst for N-Acylation of Sulfonamides under Heterogeneous and Solvent-free Conditions. Journal of the Iranian Chemistry Society 6: 405–411.
• 27. Massah A R, Asadi B, Hoseinpour M, Molseghi A, Kalbasi R J & Naghash H J (2009). A novel and efficient solvent-free and heterogeneous method for the synthesis of primary, secondary and bis-N-acylsulfonamides using metal hydrogen sulfate catalysts. Tetrahedron 65: 7696–7705.
• 28. Morisawa Y, Kataoka M, Nagahori H, Sakamoto T, Kitano N, Kusano K & Sato K (1980). Studies on Anticoccidial Agents. 13. Synthesis and Anticoccidial Activity of Nitropyridine-2-and-3-sulfonamides and Derivatives. Journal of Medicinal Chemistry 23: 1376–1380.
• 29. Musser J H, Kreft A F, Bender R H W, Kubrak D M, Grimes D, Carlson R P, Hand J M & Chang J (1990). N-[(Arylmethoxy)phenyl] carboxylic acids, hydroxamic acids, tetrazoles, and sulfonyl carboxamides. Potent orally active leukotriene D4 antagonists of novel structure. Journal of Medicinal Chemistry 33: 240–245.
• 30. Reddy C R, Mahipal B & Yaragorla S R (2007). A new and efficient method for the facile synthesis of N-acyl sulfonamides under Lewis acid catalysis. Tetrahedron Letters 48: 7528–7532.
• 31. Singh S K, Vobbalareddy S, Kalleda S R, Casturi S R, Mullangi R, Ramanujam R, Yeleswarapu K R & Iqbal J (2006). N-Acylated sulfonamide sodium salt: A prodrug of choice for the bifunctional 2-hydroxymethyl-4-(5-phenyl-3-trifluoromethylpyrazol-1-yl) benzenesulfonamide class of COX-2 inhibitors. Bioorganic & Medicinal Chemistry Letters 16: 3921–3926.
• 32. Singh D U, Singh P R & Samant S D (2004). Fe-exchanged montmorillonite K10-the first heterogeneous catalyst for acylation of sulfonamides with carboxylic acid anhydrides. Tetrahedron Letters 45: 4805–4807.
• 33. Wang Y, Soper D L, Dirr M J, Delong M A, De B & Wos J A (2000). The Synthesis and Human FP Receptor Binding Affinity of 13, 14-Dihydro Prostaglandin F1α Sulfonamides: Potential Treatments for Osteoporosis. Chemical Pharmaceutical Bulletin 48: 1332–1337.
• 34. Wang Y, Sarris K, Sauer D R & Djuric S W (2007). An expeditious and convenient synthesis of acylsulfonamides utilizing polymer-supported reagents. Tetrahedron Letters 48: 5181–5184.
• 35. Queen A (1967). Kinetics of the hydrolysis of acyl chlorides in pure water. Canadian Journal of Chemistry 45: 1619-1629.