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Efficient, Scalable and Economical Preparation of Tris(deuterium)- And 13C-labelled N-methyl-N-nitroso-p-toluenesulfonamide (Diazald®) and Their Conversion to Labelled Diazomethane

Efficient, Scalable and Economical Preparation of Tris(deuterium)- And 13C-labelled N-methyl-N-nitroso-p-toluenesulfonamide (Diazald®) and Their Conversion to Labelled Diazomethane

Samuel W J Shields, Jeffrey M Manthorpe

J Labelled Comp Radiopharm. 2014 Oct;57(12):674-9.

PMID: 25318972

Abstract:

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

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP1156508869	Ipronidazole-OH-(N-methyl-d3)	1156508-86-9	Price
AP14742268	Methanol-13C	14742-26-8	Price
AP32479984	Methanol-13C,d4	32479-98-4	Price

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