3-Mercaptopropionic Acid → 2-(2,4-dichlorophenyl)-3-(2-carboxyethylthio)-1-(1H-1,2,4-triazol-1-yl)-propan-2-ol

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Reaction Conditions

Reaction Steps

3-Mercaptopropionic acid (1.2 g, 1.1 equiv.) was dissolved in dimethylformamide (50 ml) and cooled to 5° C. in an ice bath. Sodium hydride (1.6 g of a 50% dispersion in oil, 3.3 equiv.) was added in portions over 10 minutes, followed by 2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane mesylate (3.6 g). After stirring overnight (19 hours) the mixture was poured onto ice (200 ml) and extracted with methylene chloride (3×50 ml). The aqueous layer was adjusted to pH3 with hydrochloric acid (5N) and extracted with methylene chloride (3×50 ml). The organic extracts were combined, washed with saturated sodium chloride solution (2×50 ml), dried (Na2SO4), and evaporated under reduced pressure to a gum, 5.6 g.

Provenance & Evidence