41178-58-9

Upstream product

• 78-81-9 isobutylamine 
• 98-09-9 benzenesulfonyl chloride 
• 110-96-3 diisobutylamine 
• 873-55-2 sodium benzenesulfonate 
• 6093-51-2 chloro-diisobutyl-amine 
• 2955-86-4 N¹,N¹,N²,N²-tetraisobutylethane-1,2-diamine 
• 108-86-1 bromobenzene 
• 1308074-49-8 2-bromo-N,N-diisobutylbenzenesulfonamide 

Relevant academic research and scientific papers

Charge-Transfer Complex Promoted Regiospecific C?N Bond Cleavage of Vicinal Tertiary Diamines

A catalyst-free, charge-transfer complex promoted coupling of sulfonyl chlorides with vicinal tertiary diamines to generate sulfonamides is presented. Mechanistic studies showed that these reactions are proceeded via charge transfer of vicinal tertiary diamines to sulfonyl chlorides, forming the unstable sulfonyl quaternary ammonium like complexes which induced the regiospecific intramolecular C?N bond cleavage of vicinal tertiary diamines. (Figure presented.).

Palladium-catalysed dehydrogenative sp3 C-H bonds functionalisation into alkenes: A direct access to N-alkenylbenzenesulfonamides

The palladium-catalysed dehydrogenation of sp3 carbon-hydrogen bonds of N-alkylbenzenesulfonamides allows a simple access to N-alkenylbenzenesulfonamides. The reaction proceeds with easily accessible catalysts, with pivalate as a base, and allo

Benzenesulfonyl chloride with primary and secondary amines in aqueous media - Unexpected high conversions to sulfonamides at high pH

We have determined pH-yield profiles under pseudo-first-order conditions of the reactions of benzenesulfonyl chloride with a set of primary and secondary water-soluble alkylamines, and have found with certain amines, such as dibutylamine, a profile taking the form of a sigmoid pH-yield curve with relatively high yields of the sulfonamide persisting with increasing basicity up to and including 1.0 mol/L sodium hydroxide. This behaviour is quantitatively accounted for by invoking, in addition to the usual second-order reaction of the sulfonyl chloride with the amine, two third-order terms (i) one first-order in sulfonyl chloride, amine and hydroxide anion, and (H) another first-order in sulfonyl chloride and second-order in the amine. The importance of the third-order terms correlates approximately with the total number of alkyl carbon atoms in the amine, and this in turn is regarded as related to the hydrophobic character of the amine. Experiments to test this picture included: (i) observation of a bell-shaped curve with bis(2-methoxyethyl)amine, (H) in the reaction of dibutylamine in THF-H2O (1:1), and also (iii) in the reaction of dibutylamine in 1.0 mol/L tetrabutylammonium bromide, and (iv) increase in the contributions of the third-order terms in 1.0 mol/L aqueous sodium chloride. Preparative reactions with dibutylamine, 1-octylamine, and hexamethylenimine in 1.0 mol/L aqueous sodium hydroxide with a 5% excess of benzenesulfonyl chloride gave, respectively, 94%, 98%, and 97% yields of the corresponding sulfonamides.

Chemistry of Organic Chloramines. Formation of Arenesulfonamides by Derivatization of Organic Chloramines with Sodium Arenesulfinates

Organic chloramines react rapidly with sodium benzenesulfinate or sodium toluenesulfinate to form arenesulfonamides.Derivatization was carried out by three different methods, one involving derivatization of pure chloramines and two involving derivatization of the chloramines generated in situ by reaction of the amine with sodium hypochlorite.Seventeen arenesulfonamides whose amine precursors included primary and secondary aliphatic amines, aromatic amines, and amino acids were synthesized in poor to excellent yields depending on the method used.Effects of structure,stability, and water solubility of the chloramine precursors are discussed.Benzenesulfonyl chloride can be isolated from the reaction of 10-4 M N-chloropiperidine with sodium benzenesulfinate.Competing hydrolysis of the sulfonyl chloride accounts for low yields of sulfonamide for dilute solutions of chloramine.