146475-54-9

Usage

Uses

Used in Organic Synthesis:
N,N-Dimethyl-cyclopropanesulfonamide is used as a reagent in organic synthesis for its capacity to engage in various chemical reactions, including cycloadditions and ring-opening reactions, which are essential for constructing complex organic molecules.
Used in Pharmaceutical and Agrochemical Preparation:
In the pharmaceutical and agrochemical industries, N,N-Dimethyl-cyclopropanesulfonamide is utilized as a key intermediate due to its versatile reactivity and compatibility with different functional groups, contributing to the development of new drugs and agrochemical products.
Used in Metal-Catalyzed Reactions:
As a ligand in metal-catalyzed reactions, N,N-Dimethyl-cyclopropanesulfonamide is employed to enhance the efficiency and selectivity of these reactions, which is crucial for the synthesis of specific organic compounds with desired properties.
Used in the Synthesis of Diverse Organic Compounds:
Recognized as a valuable building block, N,N-Dimethyl-cyclopropanesulfonamide is used in the synthesis of a wide range of organic compounds, showcasing its importance in expanding the scope of organic chemistry and its applications across various fields.

InChI:InChI=1/C5H11NO2S/c1-6(2)9(7,8)5-3-4-5/h5H,3-4H2,1-2H3

Upstream product

• 78472-00-1 3-chloro-propane-1-sulfonic acid dimethylamide 
• 139631-62-2 cyclopropanesulfonyl chloride 
• 124-40-3 dimethyl amine 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 2083-91-2 N,N-Dimethyltrimethylsilylamine 

Relevant academic research and scientific papers

Condensed tricyclic compound and applications in medicines

The invention relates to a condensed tricyclic compound and applications in medicines, particularly to applications of the condensed tricyclic compound as drugs for treating and/or preventing hepatitis B, specifically to a compound represented by general

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.).

Preparation of sulfonamides from N-silylamines

Sulfonamides have been prepared in high yields by the reactions of N-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from the sulfonyl chloride with aminotriphenyl silane (Ph3SiNH2), a conversion demonstrated with the synthesis of the carbonic anhydrase inhibitor, acetazolamide.

Cyclopropanesulfonyl Chloride: Its Mechanism of Hydrolysis and Reactions with Tertiary Amines in Organic Media

Cyclopropanesulfonyl chloride (1) has been synthesized and its reactions examined to see if the three-membered ring leads to unusual reactions in either 1 or the corresponding sulfene, cyclopropanethione S,S-dioxide (2). pH-rate profiles, primary kinetic isotope effects (KIE's), and pH-product ratio experiments are in full agreement with mechanisms of hydrolysis of 1 like those of a simple alkanesulfonyl chlorides (J.Am.Chem.Soc.1992,114,1743-1749), specifically, (a) below pH 7.2 by SN2-S reaction with water and (b) above pH 7.3, elimination by hydroxide to form the sulfene (2) which is trapped by (i) water below pH 12.0 and (ii) hydroxide above pH 12.0.The products of the reaction of cyclopropanesulfonyl-1-d chloride (9) with triethylamine and 2-propanol in dichloromethane indicate that most of the reaction goes via 2; the analogous reaction with trimethylamine apparently proceeds by a direct formation of the sulfonylammonium chloride (14) which then yields the α-deuterated N,N-dimethyl sulfonamide (12, R=Me).The evident sulfene formation processes in the reaction of triethylamine with ethenesulfonyl, 2-propanesulfonyl, and cyclopropanesulfonyl chlorides show very low primary KIE's (1.5), pointing to highly product-like transition states.Reaction of 1 with an enamine (1-pyrrolidino-2-methylpropene, 20) in the presence of a base in either water or dichloromethane gave cyclopropanesulfonpyrrolidide (23) and an aldehyde adduct (24), but no four-membered cycloadduct (21).