N-Sulfonylation of amines, imides, amides and anilides using p-TsCl in presence of atomized sodium in EtOH–THF under sonic condition

Abstract

a b s t r a c tA simple, facile and an efficient procedure for the N-sulfonylation of amines, imides, amides and anilides using p-TsCl in the presence of atomized sodium in a mixture of EtOH-THF under sonic condition is developed. The method is rapid, mild and inexpensive; yields are high and the reactions go to completion within 2-8 min.

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

“…From these studies emerged the important role played by acylsulfonamide moiety: It represents not only a bioisosteric replacement of carboxylic acid, but also it establishes good interactions within EP 3 receptor. Several new EP 4 antagonists show acylsulfonamide structure: GW-627368X (22) and BGC-20-1531 (23) are benzenesulfonamide derivatives with high EP 4 affinity. It is also implicated in pathological conditions, such as cancer growth and metastasis, and in some inflammatory diseases.…”

Synthesis and Antibacterial Activity of Benzazolyl Azolyl Sulfamoyl Acetamides

“…The sufonylation of heteroarylamines was reported by several methods . Recently, we have reported N ‐sulfonylation reaction in the presence of dispersed sodium where in the reaction proceeded at a faster rate with high yields . In fact, the reaction of 1 with methyl 2‐(chlorosulfonyl)acetate ( 4 ) in the presence of dispersed sodium under ultrasonication gave methyl 2‐( N ‐(4‐(4‐thiophen‐2‐yl)oxazol‐2‐yl)sulfamoyl)acetate ( 5 ) in excellent yield.…”

Synthesis of Amido Sulfonamido Heteroaromatics Under Ultrasonication and Their Antimicrobial Activity

“…The same reaction under ultrasonic irradiation proceeded at a faster rate but there is no improvement in the yield of the product ( Table ). The literature survey indicated that N ‐sulfonylation of imidazoles and benzimidazoles is accomplished in the presence of sodium in polar solvents under ultrasonication . Moreover, a variety of organic reactions are performed to get the desired molecules by employing sodium in polar solvents under sonication .…”

“…Recently, the use of fine dispersed sodium (atomized sodium) attains importance since the reaction proceeds at a faster rate in the presence of dispersed sodium . Hence, the reaction between 1a and 2 is performed in the presence of dispersed sodium.…”

“…The literature survey indicated that N-sulfonylation of imidazoles and benzimidazoles is accomplished in the presence of sodium in polar solvents under ultrasonication. [42] Moreover, a variety of organic reactions are performed to get the desired molecules by employing sodium in polar solvents under sonication. [31] In our endeavor to develop an efficient and simple method for N-sulfonylation of heteroaryl amines, different solvents are used to ascertain the suitable solvent for the reaction between 1a and 2 in the presence of sodium.…”