1,4-Dioxane → HCID 86610487, compound

Participants

Reaction Conditions

Reaction Steps

In an oven-dried, 100-mL, round-bottomed flask was placed thioisonicotinamide (Pflaltz-Bauer) (2.9 g, 21 mmol) in 1,4-dioxane (60 mL). Methyl 4-chloroacetoacetate (Aldrich, 3.16 g, 2.4 mL, 21 mmol) was added at RT. The flask was purged with N2 and the solution was heated to 75° C. for 12 h. The mixture was cooled to RT, quenched with 2N NH3 in MeOH (10 mL), and concentrated. The material was purified by flash chromatography on silica gel (EtOAc/hexane, 50:50) to afford 2-(4-pyridyl)-thiazole acetic acid methyl ester as a light yellow solid. Mp: 78-79° C. MS m/z: 235 (M+1). Calc'd for C11H10N2O2S: 234.05.

Provenance & Evidence