19299-41-3

Upstream product

• 74-89-5 methylamine 
• 1939-99-7 benzenesulfonyl chloride 
• 89873-37-0 4-hydroxy-2-methyl-5-phenyl-3(2H)-isothiazolone 1,1-dioxide 
• 57864-65-0 sodium salt of phenylmethanesulfamide 
• 74-88-4 methyl iodide 
• 675622-48-7 O-benzylsulfonyl-N-[phenyl(1-phenylethyl)phosphinoyl]hydroxylamine 
• 950017-96-6 C₁₆H₁₉NO₃S 
• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 
• 4563-33-1 phenyl-methanesulfonic acid amide 
• 67-56-1 methanol 
• 57267-76-2 sodium α-toluenesulfonate 

Downstream Products

• 106003-76-3 N-methyl-N'-(2,7-octadienyl)-phenylmethanesulfamide 
• 89873-37-0 4-hydroxy-2-methyl-5-phenyl-3(2H)-isothiazolone 1,1-dioxide 
• 85952-29-0 (4-nitro-phenyl)-methanesulfonic acid methylamide 
• 803727-96-0 N-methyl-N-(dimethyl-tert-butylsilyl)-1-phenylmethanesulfonamide 
• 885373-76-2 N-(cyclohexylmethyl)-1-phenylmethanesulfonamide 
• 2154-56-5 benzyl radical 
• 116043-33-5 N-Methyl-N-((E)-octa-2,7-dienyl)-C-phenyl-methanesulfonamide 

Relevant academic research and scientific papers

Acyl vs Sulfonyl Transfer in N-Acyl β-Sultams and 3-Oxo-β-sultams

(Matrix presented) N-Acylsulfonamides usually react with nucleophiles by acyl transfer and C-N bond fission. However, the hydrolysis of N-acyl β-sultams is a sulfonyl transfer reaction that occurs with S-N fission and opening of the four-membered ring. Similar to other β-sultams, the N-acyl derivatives are at least 106-fold more reactive than N-acyl sulfonamides. 3-Oxo-β-sultams are both β-lactams and β-sultams but also hydrolyze with preferential S-N bond fission.

Copper-catalyzed oxidative methylation of sulfonamides by dicumyl peroxide

A novel and facile copper-catalyzed methylation of sulfonamides was herein demonstrated. The practical transformation took place readily under the oxidative conditions, and N-methyl amides (23 examples) were successfully furnished in high efficiency (up to 90% yields). Dicumyl peroxide was considered to act not only as the oxidant in the system, but also methyl donor for the methylation protocol.

N-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal-Ligand Bifunctional Ruthenium Catalyst [(p-cymene)Ru(2,2′-bpyO)(H2O)]

A ruthenium complex [(p-cymene)Ru(2,2′-bpyO)(H2O)] was found to be a general and efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate salt. Moreover, a series of sensitive substituents, such as nitro, ester, cyano, and vinyl groups, were tolerated under present conditions. It was confirmed that OH units in the ligand are crucial for the catalytic activity. Notably, this research exhibited the potential of metal-ligand bifunctional ruthenium catalysts for the hydrogen autotransfer process.

Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonate

An iridium complex Cp*Ir@CTF, which is synthesized by the coordinative immobilization of [Cp*IrCl2]2 on a functionalized covalent triazine framework (CTF), was found to be a general and highly efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate. Under environmentally benign conditions, a variety of desirable products were obtained in high yields with complete selectivities and functional group friendliness. Furthermore, the synthesized catalyst could be recycled by simple filtration without obvious loss of catalytic activity after sixth cycle. Notably, this research exhibited the potential of covalent triazine framework-supported transition metal catalysts for hydrogen autotransfer process.

Method for synthesizing N-methyl sulfonamide in water

The invention discloses a method N - for synthesizing,methylsulfamide in water, by using a transition metal iridium catalyst to catalyze N - methylation reaction. by using a non-toxic and harmless water as a solvent, to avoid using the organic agent; to react only as a byproduct, without an environmental hazard; reaction temperature with respect to the previous strip more mild; and have a wide application prospect; with high selectivity, reaction atomic economy.

N-Methylation of Amines with Methanol in Aqueous Solution Catalyzed by a Water-Soluble Metal-Ligand Bifunctional Dinuclear Iridium Catalyst

The N-methylation of amines with methanol in aqueous solution was proposed and accomplished by using a water-soluble metal-ligand bifunctional dinuclear iridium catalyst. In the presence of [(Cp*IrCl)2(thbpym)][Cl]2 (1 mol %), a range of desirable products were obtained in high yields under environmentally benign conditions. Notably, this research exhibited the potential of transition metal-catalyzed activation of methanol as a C1 source for the construction of the C-N bond in aqueous solution.

N-Methylation of Amines with Methanol Catalyzed by a Cp?Ir Complex Bearing a Functional 2,2′-Bibenzimidazole Ligand

A new type of Cp?Ir complex bearing a functional 2,2′-bibenzimidazole ligand was designed, synthesized, and found to be a highly effective and general catalyst for the N-methylation of a variety of amines with methanol in the presence of a weak base (0.3 equiv of Cs2CO3).

A useful Pd-catalyzed Negishi coupling approach to benzylic sulfonamide derivatives

(Chemical Equation Presented) A mild catalytic system to access diversely functionalized benzylic sulfonamides has been developed. Palladium-catalyzed α-arylation by Negishi cross-coupling of sulfonamide-stabilized anions and a wide range of aryl iodides, bromides, and triflates constitutes a practical strategy for the synthesis of various benzylic sulfonamides.

Synthesis of α-fluorosulfonamides by electrophilic fluorination

(Chemical Equation Presented) α-Fluorosulfonamides were prepared by electrophilic fluorination of tertiary sulfonamides using N- fluorobenzenesulfonimide as fluorinating agent and utilizing the dimethoxybenzyl group (DMB) as a new sulfonamide protecting g

Competing sulfonylation and phosphonylation following rearrangement of an O-sulfonyl-N-phosphinoylhydroxylamine with tert-butylamine: Demonstration of a phosphonamidic-sulfonic anhydride intermediate and 18O-labelling evidence on how it may be formed

Reaction of R(Ph)P(O)NHOSO2Bn (R = PhMeCH) with Bu tNH2 in CH2Cl2 gives a mixture of RP(O)(NHPh)NHBut and ButNHSO2Bn, the proportion of the sulfonamide increasing steadily (14.6% to 32.9%) as the concentration of amine is reduced (8.0 to 0.2 mol dm-3). Apparently the phenyl and sulfonate groups in the substrate become transposed, giving a phosphonamidic-sulfonic anhydride RP(O)(NHPh)OSO2Bn which then reacts at the phosphorus or sulfur atom to give the final products; an authentic sample of the anhydride gives similar mixtures of products. Substrate labelled with 18O in the sulfonyl position (57 mol% one 18O atom) gives sulfonamide containing most but not all of the label (43.7 mol% one 18O atom with 2.0 mol dm-3 amine). This implies partial equilibration of the three sulfonate oxygen atoms during rearrangement, or after the anhydride intermediate has been formed.