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p-Toluene sulfonamide was used to prepare the precursor required for synthesis of ethyl 6-phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate. It act as a derivative of ammonia activated to alkylation by alkyl halides is exemplified by the synthesis of N-tosyl-2,3-dihydroisoindole from o-xylylene dibromide. It is a precursor of N-tosyl imines.
Kui Lu; Ohyun Kwon. Phosphine-Catalyzed [4+2] Annulation: Synthesis of Ethyl 6-Phenyl-1-Tosyl-1,2,5,6-Tetrahydropyridine-3-Carboxylate. Organic Syntheses. 2009, 2009 (86), 212-224.
D. S. Tarbell; Clay Weaver. The Condensation of Sulfoxides with p-Toluenesulfonamide and Substituted Acetamides. J. Am. Chem. Soc. 1941, 63 (11), 2939-2942.
Use of p-toluenesulfonamide as a derivative of ammonia activated to alkylation by alkyl halides is exemplified by the synthesis of N-tosyl-2,3-dihydroisoindole from o-xylylene dibromide: Org. Synth. Coll., 5, 1064 (1973). Similarly, has been used as the precursor of nitrogen-containing crown ethers; see, e.g.: J. Org. Chem., 53, 5292 (1988).
Precursor of N-tosyl imines, which are useful intermediates in synthesis: Synlett, 2097 (2003).
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.