Chloroacetic Acid → Acetic acid, [(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)thio]-

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Reaction Conditions

Reaction Steps

A mixture of 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-thiol (1.0 g, 5.6 mmol), sodium hydroxide (0.44 g, 11.1 mmol), and water (22 mL) was added to a 100 mL RBF with a magnetic stirring bar. The flask was fitted with a condenser, and the mixture was warmed to reflux in a 120° C. oil bath for 30 min. The mixture was removed from the oil bath and allowed to cool, and chloroacetic acid (0.525 g, 5.6 mmol) was added. Warming to reflux was continued for 6 h. The mixture was allowed to cool to ambient temperature, and the pH was adjusted to 2 with 1 M aqueous hydrochloric acid (5 mL). A solid precipitate was isolated by filtration, rinsed with 1 M hydrochloric acid (2 mL) and water (5 mL), and allowed to dry. The title compound was obtained as a tan solid (1.16 g, 88% yield). 1H NMR (DMSO-d6, 400 MHz) δ ppm: 12.85 (br s, 1H), 7.12 (s, 1H), 4.08 (s, 2H), 2.66 (s, 3H), 2.54 (s, 3H).

Provenance & Evidence