21992-47-2

Basic information

• Product Name: N-[ethyl(methyl)-lambda~4~-sulfanylidene]-4-methylbenzenesulfonamide
• Synonyms: N-[ethyl(methyl)-lambda~4~-sulfanylidene]-4-methylbenzenesulfonamide
• CAS NO: 21992-47-2
• Molecular Formula: C₁₀H₁₅NO₂S₂
• Molecular Weight: 245.3616
• Mol File: 21992-47-2.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-[ethyl(methyl)-lambda~4~-sulfanylidene]-4-methylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[ethyl(methyl)-lambda~4~-sulfanylidene]-4-methylbenzenesulfonamide(21992-47-2)
• EPA Substance Registry System: N-[ethyl(methyl)-lambda~4~-sulfanylidene]-4-methylbenzenesulfonamide(21992-47-2)

Safety Data

• Hazardous Substances Data: 21992-47-2(Hazardous Substances Data)

Upstream product

• 624-89-5 Ethyl methyl sulfide 
• 127-65-1 chloroamine-T 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 70-55-3 toluene-4-sulfonamide 

Relevant articles and documents

Catalytic Asymmetric Sulfimidation

A direct catalytic imidation of sulfides to sulfimides with [N-(p-tolylsulfonyl)imino]phenyliodinane (TsN=IPh) using a catalytic amount of copper triflate (CuOTf) has been developed. The reaction proceeds with a wide range of sulfides to give the corresponding sulfimides in 50-83% isolated yields. When the reaction is applied to allylic sulfides, the products are the corresponding sulfonamides produced via [2,3] sigmatropic rearrangement of the initially formed allylic sulfimides. In the presence of a chiral bis(oxazoline) as ligand, asymmetric induction occurs to afford the chiral sulfimides (up to 71% ee) and sulfonamides (up to 58% ee). Chloramine T (TsNClNa) can be used in place of TsN=IPh for asymmetric sulfimidation, but the ee's are much lower. Some mechanistic observations are described.