Hydrochloric Acid → 4-[3-(3-Fluoro-4-methyl-phenyl)-4,4-dimethyl-5-oxo-2-thioxo-imidazolidin-1-yl]-phthalonitrile

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Reaction Conditions

Reaction Steps

A mixture of 3k (370 mg, 2 mmol, prepared by a method similar to the synthesis of 3d) and 6h (384 mg, 2 mmol, prepared by a method similar to the synthesis of 6b) in DMF (10 mL) was heated under microwave irradiation at 150° C. for 5 h. To this mixture was added ethanol (10 mL) and aqueous HCl solution (2N, 5 mL). The resulting mixture was heated at reflux for 1 h. The solution was poured into ice-cold water and extracted with ethyl acetate (3×30 mL). The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The residue was purified with Pre-HPLC, affording the title compound (Example 25, 150 mg, 19.8% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.93-7.91 (m, 2H), 7.26-7.09 (m, 3H), 2.35 (s, 3H), 1.58 (s, 6H). ESI-MS (M+H)+: 379.

Provenance & Evidence