Abstract
The amidomethylation (Tscherniac-Einhorn) reaction of the anthraquinones I-III (R = II) was examined in an attempt to introduce 3-halogenopropionamidomethyl groups into dyes for subsequent conversion into isothiuronium salt dyes. Methods described in the literature using 3-halogenopropionamides or propionitriles and various formaldehyde sources gave poor yields due to the reaction of formaldehyde with the anthraquinones. Satisfactory methods have been developed using bis(chloromethyl)ether to amidoalkylate I-III (R = H). Reaction of the 3-bromo- or 3-iodopropionamido-methyl derivatives of I-III (R = H) with thiourea or tetramethylthiourea gave poor yields of unstable isothiuronium salts, which were unsatisfactory wool dyes.
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