13707-48-7

Basic information

• Product Name: Benzenesulfonamide, 4-methyl-N-(2-pyridinylmethylene)-
• CAS NO: 13707-48-7
• Molecular Formula: C13H12N2O2S
• Molecular Weight: 260.316
• Mol File: 13707-48-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, 4-methyl-N-(2-pyridinylmethylene)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 4-methyl-N-(2-pyridinylmethylene)-(13707-48-7)
• EPA Substance Registry System: Benzenesulfonamide, 4-methyl-N-(2-pyridinylmethylene)-(13707-48-7)

Safety Data

• Hazardous Substances Data: 13707-48-7(Hazardous Substances Data)

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 70-55-3 toluene-4-sulfonamide 
• 586-98-1 2-Hydroxymethylpyridine 

Downstream Products

• 134542-02-2 (E)-2-(buta-1,3-dien-1-yl)pyridine 
• 538-49-8 (Z)-2-(2-phenylethenyl)pyridine 
• 1370281-69-8 C₁₉H₂₅BN₂O₄S 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 568588-94-3 [[[1-(tert-butyldimethylsilyl)-1H-indol-3-yl](pyridin-2-yl)methyl]-(toluene-4-sulfonyl)amino]acetic acid ethyl ester 
• 452897-60-8 N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl]pyridin-2-ylmethyl]-4-methylbenzenesulfonamide 

Relevant articles and documents

A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N -Sulfonyl imines

The Wittig reaction involving direct olefination of triphenylphosphonium ylides (Ph3PCHR) with aldehydes is arguably the most often used method for alkene synthesis, but in general it yields mixtures of Z- and E-alkenes for semistabilized triphenylphosphonium ylides (R = aryl or vinyl). We have developed a simple and efficient protocol to improve the stereoselectivity significantly by replacing the aldehydes used in the Wittig reaction with N-sulfonyl imines, which possess distinct electronic and steric properties relative to aldehydes. A broad range of aromatic, α,β-unsaturated, and aliphatic imines bearing appropriate N-sulfonyl groups smoothly undergo olefination reaction with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity. Moreover, this tunable protocol has been successfully applied to the highly stereoselective synthesis of two anticancer agents, DMU-212 and its Z-isomer.

Copper-catalyzed N-alkylation of sulfonamides with benzylic alcohols: Catalysis and mechanistic studies

The N-alkylation of sulfonamides with alcohols is efficiently performed in the presence of easily available copper catalysts via hydrogen borrowing methodology. Applying a copper acetate/potassium carbonate system the reaction of sulfonamides and alcohols gave the corresponding secondary amines in excellent yield. In situ HR-MS analysis indicated that bissulfonylated amines are formed under air atmosphere, which act as self-stabilizing Iigands for the catalytic system. UV-visible measurements suggest the interaction between the copper centre and the bissulfonylated amine. Reactions of benzyl alcohol-d 7 with p-toluenesulfonamide, Nbenzyl-p-toluenesulfonamide or N-benzylidenetoluenesulfonamide revealed that the reaction proceeds via a transfer hydrogenation mechanism and the whole process is micro-reversible. Competitive reactions of benzyl alcohol and benzyl alconol-d7 with ptoluenesulfonamide revealed a kinetic isotope effect (kH/kD) of 3.287 (0.192) for the dehydrogenation of benzyl alcohol and 0.611 (0.033) for the hydrogenation of the N-benzylidene-p-toluenesulfonamide intermediate, which suggests that dehydrogenation of the alcohol is the rate-determining step.