21896-59-3

Usage

Uses

N-(2-Chloroethyl)methanesulfonamide

InChI:InChI=1/C3H8ClNO2S/c1-8(6,7)5-3-2-4/h5H,2-3H2,1H3

Upstream product

• 151-56-4 ethyleneimine 
• 124-63-0 methanesulfonyl chloride 
• 107-06-2 1,2-dichloro-ethane 
• 689-98-5 chloroethylamine 
• 870-24-6 2-chloroethanamine hydrochloride 

Downstream Products

• 56891-61-3 4-acetamino-3-methyl-N-(β-methanesulfonamidoethyl)-N-ethylaniline 
• 92-09-1 N-{2-[(4-amino-m-tolyl)ethylamino]ethyl}methanesulfonamide 

Relevant academic research and scientific papers

Practical Synthesis of Sultams via Sulfonamide Dianion Alkylation: Application to the Synthesis of Chiral Sultams

(Equation presented) A practical synthesis of sultams was developed via intramolecular sulfonamide dianion alkylation. This method has been applied toward the synthesis of chiral sultams, which are synthetically valuable as chiral auxiliaries.

Process development of the synthetic route to sulamserod hydrochloride

Sulamserod hydrochloride is a potent S-HT4 receptor antagonist and was a clinical candidate for the treatment of gastrointestinal disorders. Process development of the fairly long synthetic route (12 linear, 14 overall steps) was undertaken. Process improvements were highlighted by aromatic chlorination choices in making dichlorobenzodioxan 2 and acetylaminochloroketone 7, a transfer hydrogenation reducing a nitro group and simultaneous aromatic dechlorination without ketone reduction to give aminoketone 5, and use of the potential mutagenic iodosulfonamide 14 to make quaternary salt 11. The chemistry was scaled-up into pilot plant reactor vessels to produce multikilogram amounts of Sulamserod hydrochloride suitable for drug development.

Method for production of N-(2-chloroethyl) methanesulfonamide

A method for the production of N-(2-chloroethyl) methanesulfonamide of high purity, which method comprises causing methanesulfonyl chloride to react with ethylene imine in the presence of ethylene dichloride and then distilling there resultant reaction mixture thereby separating therefrom N-(2-chloroethyl) methanesulfonamide, if necessary subjecting the resultant reaction mixture to extraction from water, separating the aqueous layer consequently formed, and subjecting the organic layer resulting from said extraction to distillation thereby separating N-(2-chloroetyl) methanesulfonamide.

Process for producing sulfonylamides

Sulfonylamide derivatives of the formula, wherein R is an alkyl or a phenyl group, which are particularly useful for the production of photographic chemicals, are prepared by the reaction between a sulfonylhalide of the formula, wherein R is as defined above, and X is chlorine or bromine, and 2-chloroethylamine or its salt, which is prepared by the chlorination of monoethanolamine with thionylchloride.