16358-32-0

Usage

Synthesis Reference(s)

Synthetic Communications, 18, p. 29, 1988 DOI: 10.1080/00397918808057816

InChI:InChI=1/C14H23NO2S/c1-2-3-4-5-6-10-13-15-18(16,17)14-11-8-7-9-12-14/h7-9,11-12,15H,2-6,10,13H2,1H3

Upstream product

• 111-86-4 n-Octylamine 
• 133-59-5 Toluene-2-sulfonyl chloride 
• 98-09-9 benzenesulfonyl chloride 
• 58821-20-8 N-Octanoyl-benzenesulfonamide 

Downstream Products

• 111-86-4 n-Octylamine 
• 66897-52-7 N-(2-Chloro-benzoyl)-N-octyl-benzenesulfonamide 

Relevant academic research and scientific papers

Copper-Catalyzed, N-Directed Csp3-H Trifluoromethylthiolation (-SCF3) and Trifluoromethylselenation (-SeCF3)

A direct and versatile copper-catalyzed trifluoromethylthiolation and trifluoromethylselenation of primary, secondary, and tertiary aliphatic C-H bonds was developed. The reaction provides direct access to molecules containing these emerging moieties in the presence of a wide range of common functional groups and in complex molecular environments.

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.

ROMP-generated oligomeric sulfonyl chlorides as versatile soluble scavenging agents.

[reaction: see text] A new method for homogeneous nucleophilic scavenging employing oligomeric sulfonyl chloride (OSC) reagents is described. The method utilizes OSC to rapidly scavenge a variety of amines that are present in excess. The OSC reagents are generated from ROM polymerization of 2-chlorosulfonyl-5-norbornene utilizing the second generation Grubbs catalyst to produce oligomers of varying size as stable, free-flowing powders. Following the scavenging event, these oligomers are precipitated with ethyl acetate leaving products in excellent yield and purity.

Autoinducer compounds

Autoinducer compounds which enhance gene expression in a wide variety of microorganisms, therapeutic compositions and therapeutic methods wherein gene expression within microorganisms is regulated are disclosed.

A USEFUL APPROACH TO PRIMARY AMINES

Smooth reduction of acylsulfonamides to sulfonamides by borane, when coupled to standard sulfonamide cleavage procedures, provides a general route to primary amines.