Hydrazine hydrate (1:1) → HCID 90092588, compound

Participants

Reaction Steps

To a stirred slurry of 4,4-dimethoxy-1-(1,3-thiazol-2-yl)butane-1,3-dione (8a) (1.55 g, 6.76 mmol) in ethanol (63 mL) was added dropwise hydrazine monohydrate (0.38 mL, 7.77 mmol). The mixture was stirred at room temperature overnight, then concentrated in vacuo. A saturated solution of sodium hydrogenocarbonate (8 mL) was added to the residue and the aqueous layer was extracted with ethyl acetate (2×10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The resulting solid was triturated in diethyl ether and the precipitate was filtrated. The filtrate was concentrated and the treatment was repeated as much as necessary. The combined precipitates were dried in vacuo to provide 2-[5-(dimethoxymethyl)-1H-pyrazol-3-yl]-1,3-thiazole (8b) (714 mg, 3.17 mmol, 47%) which was used without further purification.

Provenance & Evidence