158656-48-5

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 19500-02-8 2-methyl-3-methoxyaniline 

Downstream Products

• 463341-49-3 N-(3-Methoxy-2-methylphenyl)-N-methylmethanesulfonamide 
• 155960-35-3 Acetic acid 2-(benzyl-methanesulfonyl-amino)-6-methoxy-benzyl ester 
• 155960-36-4 N-Benzyl-N-(2-chloromethyl-3-methoxy-phenyl)-methanesulfonamide 
• 158656-49-6 N-Benzyl-N-(2-hydroxymethyl-3-methoxy-phenyl)-methanesulfonamide 
• 155960-38-6 N-Benzyl-N-(2-formyl-3-methoxy-phenyl)-methanesulfonamide 
• 155960-39-7 1-Benzyl-5-methoxy-1H-benzo[c][1,2]thiazine 2,2-dioxide 
• 155960-37-5 1-Benzyl-5-methoxy-3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxide 
• 155960-40-0 1-Benzyl-2,2-dioxo-1,2-dihydro-2λ⁶-benzo[c][1,2]thiazin-5-ol 
• 94794-47-5 1-Benzyl-2,2-dioxo-1,2,3,4-tetrahydro-2λ⁶-benzo[c][1,2]thiazin-5-ol 
• 88131-52-6 N-(2,2-Diethoxy-ethyl)-N-(3-methoxy-2-methyl-phenyl)-methanesulfonamide 
• 155960-34-2 N-Benzyl-N-(3-methoxy-2-methyl-phenyl)-methanesulfonamide 

Relevant academic research and scientific papers

A Convenient Synthesis of 3,4-Dihydro-2,2-Dioxide-5-Hydroxy-2,1-Benzothiazine

3-methoxy-2-methyl-aniline 3 is converted to the benzothiazine-dioxide 1 in a 7-steps procedure: the key transformation being the cyclization of an ortho-functionalized N-benzyl sulfonanilide.

Cyclization of 2-acetaldehyde Diethyl Acetals to Indoles. Evidence for Stereoelectronic Effects in Intramolecular Electrophilic Aromatic Substitution

Methanesulfonamides of N-(2,2-diethoxyethyl)anilines can be cyclized to indoles in aromatic solvents by reaction with titanium tetrachloride.The temperature of the cyclization is substituent dependent, occurring at 0 deg C for the m-methoxy derivative but requiring 130 deg C for the p-bromo compound.Yields are good for various alkoxy-, alkyl-, and haloindoles, ranging from 60percent to 90percent.Meta-substituted reactants give rise to mixtures of 4- and 6-substituted indoles in which the 6-substituted product dominates by 2-4:1.The cyclization fails for ortho-substituted reactants.The major reaction process is N-dealkylation in the case of ortho-substituted compounds.An analogous cyclization occurs with the methanesulfonamides of N-(3,3-diethoxypropyl)anilines to give 1-(methylsulfonyl)-4-chloro-1,2,3,4-tetrahydroquinolines.This cyclization is much more rapid than for the five-membered ring closure leading to indoles and indicates a substantial rate retardation due to stereoelectronic effects in the indole cyclization.Ortho substitution also prevents cyclization in the six-membered-ring case.