Issue 4, 2011

Facile N-alkylation of acridineesters with 1,3-propane sultone in ionic liquids

Abstract

Hydrophilic chemiluminescent acridinium esters containing N-sulfopropyl groups are extremely useful labels in the clinical diagnostics industry. The synthesis of these labels is normally accomplished by N-alkylation of the acridine ester precursors with the carcinogenic reagent 1,3-propane sultone in neat reactions where the alkylating reagent also serves as the solvent. Product yields are often poor, the reactions are not reproducible and are also difficult to scale-up. In our efforts to develop a greener and a more efficient synthesis of N-sulfopropyl acridinium esters, we have discovered that commonly used room temperature ionic liquids such as [BMIM][BF4] and [BMIM][PF6] are excellent media for the N-alkylation of poorly reactive acridine esters with 1,3-propane sultone. Advantages include a significant reduction in the amount of toxic 1,3-propane sultone needed for good conversion to product, and minimal formation of polysulfonated products. The alkylation reaction in ionic liquids is amenable to scale-up for the synthesis of gram quantities of hydrophilic, chemiluminescent acridinium esters.

Graphical abstract: Facile N-alkylation of acridine esters with 1,3-propane sultone in ionic liquids

Article information

Article type
Paper
Submitted
01 Nov 2010
Accepted
23 Dec 2010
First published
09 Feb 2011

Green Chem., 2011,13, 913-921

Facile N-alkylation of acridine esters with 1,3-propane sultone in ionic liquids

A. Natrajan and D. Wen, Green Chem., 2011, 13, 913 DOI: 10.1039/C0GC00758G

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