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Synthesis of 11C-labelled N,N'-diphenylurea and Ethyl Phenylcarbamate by a Rhodium-Promoted Carbonylation via [11C]isocyanatobenzene Using Phenyl Azide and [11C]carbon Monoxide

Synthesis of 11C-labelled N,N'-diphenylurea and Ethyl Phenylcarbamate by a Rhodium-Promoted Carbonylation via [11C]isocyanatobenzene Using Phenyl Azide and [11C]carbon Monoxide

Hisashi Doi, Julien Barletta, Masaaki Suzuki, Ryoji Noyori, Yasuyushi Watanabe, Bengt Langstrom

Org Biomol Chem. 2004 Nov 7;2(21):3063-6.

PMID: 15505707

Abstract:

The reaction with phenyl azide and [11C]carbon monoxide to give N,N'-diphenyl[11C]urea and ethyl phenyl[11C]carbamate has been studied with the aim of development of a new methodology for carbonylation using [11C]carbon monoxide with high specific radioactivity. The synthesis of 11C-labelled N,N'-diphenylurea from phenyl azide and [11C]carbon monoxide, with 1,2-bis(diphenylphosphino)ethane-bound Rh(I) complex at 120 degrees C at a pressure of 35 MPa in the presence of aniline was accomplished in 82% trapping efficiency and 82% conversion yield. This approach was also useful for the synthesis of ethyl phenyl[11C]carbamate with lithium ethoxide as a nucleophilic reagent giving 90% trapping efficiency and 76% conversion yield. These reactions can be considered to proceed via a [11C]isocyanate or a [11C]isocyanate-coordinated Rh complex to give the corresponding 11C-products. This protocol provides the chemical basis for the synthesis of [11C]urea and [11C]carbamate derived from [11C]isocyanates.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2388070-A	Lithium ethoxide		2388-07-0	Price

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