85894-45-7

Upstream product

• 811-98-3 d⁽⁴⁾-methanol 
• 70-55-3 toluene-4-sulfonamide 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 1407505-98-9 N-methyl-d₃ tert-butyl para-toluenesulfonylcarbamate 

Downstream Products

• 42366-72-3 N-methyl-d₃-N-nitroso-para-toluenesulfonamide 

Relevant academic research and scientific papers

Efficient, scalable and economical preparation of tris(deuterium)- and 13C-labelled N-methyl-N-nitroso-p-toluenesulfonamide (Diazald) and their conversion to labelled diazomethane

A method for the preparation of multi-gramme quantities of N-methyl-d3-N-nitroso-p-toluenesulfonamide (Diazald-d3) and N-methyl-13C-N-nitroso-p-toluenesulfonamide (Diazald-13C) and their conversion to diazomethane-d2 and diazomethane-13C, respectively, is presented. This approach uses robust and reliable chemistry, and critically, employs readily commercially available and inexpensivemethanol as the label source. Several reactions of labelled diazomethane are also reported, including alkene cyclopropanation, phenolmethylation and α-diazoketone formation, as well as deuteriumscrambling in the preparation of diazomethane-d2 and subsequent methyl esterification of benzoic acid.

Manganese-Catalyzed N-Alkylation of Sulfonamides Using Alcohols

An efficient manganese-catalyzed N-alkylation of sulfonamides has been developed. This borrowing hydrogen approach employs a well-defined and bench-stable Mn(I) PNP pincer precatalyst, allowing benzylic and simple primary aliphatic alcohols to be employed as alkylating agents. A diverse range of aryl and alkyl sulfonamides undergoes mono-N-alkylation in excellent isolated yields (32 examples, 85% average yield).