Download PDF
Synthesis 1986; 1986(4): 336-337
DOI: 10.1055/s-1986-31607
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A Convenient Synthetic Route to 2,2′-Biimidazole

Donald P. Matthews* , Jeffrey P. Whitten, James R. Mccarthy
  • *Merrell Dow Research Institute, Indianapolis Center, Indianapolis, Indiana 46268, U. S. A.
Further Information

Publication History

Publication Date:
27 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Convenient two step procedures for the synthesis of 2,2′-biimidazole (3)and its dihydrochloride salt (4) starting with bis-methylimidate (1) in an overall yield of 72 and 83%, respectively, are reported. Bis-methylimidate(1) was treated with two equivalents of aminoacetaldehyde dimethyl acetal underacid-catalyzed conditions to provide bis-N-(2,2-dimethoxyethylacetamidine)dihydrochioride (2) in 84% yield. Fusion of 2 with an equivalent of p toluenesulfonic acid at 200°C gave 3 in 86% yield. Alternatively, 2 was refluxed with 5 molar hydrochloric acid to provide 4 as well as 3 in combined yield of 99%. Evidence is presented for the intermediacy of 2-[4(5)-methoxy-2-imidazolyl]imidazole (5) in the formation of the title compound. Water-soluble 4 is converted to 3 by treatment with potassium carbonate.