Substituted 2-mercapto-imidazoles and their preparation

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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548321, 549379, C07D40106, C07D23384

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active

045843830

ABSTRACT:
The invention provides novel 1-substituted-5-hydroxymethyl-2-mercapto-imidazoles of the formula ##STR1## wherein R is pyridylmethyl, alkyl of 1 to 4 carbon atoms, or a radical of formula: ##STR2## in which R.sub.1 is hydrogen or halogen and n is 1-3. These compounds are prepared by reacting together dihydroxyacetone dimer, the amine R--NH.sub.2, and potassium thiocyanate. The compounds of formula (I) are useful as starting materials in the preparation of known therapeutically valuable imidazole derivatives, by removing the mercapto group, oxidizing the alcohol group to an aldehyde group and condensing the aldehyde with an appropriate phenyl or phenylalkyl magnesium halide.

REFERENCES:
patent: 2541924 (1951-02-01), Jones
Jackman, M., et al., J. Am. Chem. Soc., 70, 2884 (1948).
L. Sattler, Adv. Carbohydr. Chemistry 3 (1948), 113.
K. Heyns et al., Z. Naturforsch. 76 (1952), 486.
F. Garcia Gonzales, et al., Anales Real. Soc. Espan. Fis. y. Quim, 44 B (1948), 233.
G. Huber et al., Helv. Chim Acta 43 (1960), 713 and 1787.
R. A. F. Bullerwell et al., J. Chem. Soc. 1951, 3030.

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