Cookies on this website

We use cookies to ensure that we give you the best experience on our website. If you click 'Accept all cookies' we'll assume that you are happy to receive all cookies and you won't see this message again. If you click 'Reject all non-essential cookies' only necessary cookies providing core functionality such as security, network management, and accessibility will be enabled. Click 'Find out more' for information on how to change your cookie settings.

Diethyl 5-amino-1-(p-methoxybenzyl)imidazole-2,4-dicarboxylate (3b) has been prepared from ethyl 2-amino-2-cyanoacetate and ethyl 1- ethoxycarbonyformimidate hydrochloride or ethyl triethoxyacetate followed by reaction with p-methoxybenzy lamine. The diester, with one equivalent of dilute sodium hydroxide solution, furnished ethyl 5-amino-1-(p-methoxybenzyl)imidazole- 4-carboxylate (7a). Diazotisation of the diester (3b) and reaction of the diazonium salt with copper(I) chloride produced diethyl 5-chloro-1-(p- methoxybenzyl)imidazole-2,4-dicarboxylate (9a) which, with dilute alkali, gave ethyl 5-chloro-1-(p-methoxybenzyl)imidazole-4-carboxylate (7b). Diazotisation of the diester (3b) in the presence of hypophosphorous acid gave diethyl-1-(p-methoxybenzyl)imidazole-2,4-carboxylate (9b) which, when hydrogenated over palladium - charcoal, produced diethyl imidazole-2,4- dicarboxylate (9c). This with bromine (chlorine) gave diethyl 5-bromo(chloro)imidazole-2,4-dicarboxylate (9d and e). The chloro derivative (9a) was similarly hydrogenated using palladium - charcoal to produce diethyl 5-chloro-imidazole-2,4-dicarboxylate (9e).

Type

Journal article

Journal

Journal of the Chemical Society, Perkin Transactions 1

Publication Date

01/12/1983

Pages

809 - 811