Hydrochloric Acid → 4-(4,4-Dimethyl-5-oxo-2-thioxo-3-p-tolyl-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 6g (348 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 24, 60 mg, 8.3% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.03 (s, 1H), 7.93 (m, 2H), 7.35 (d, J=8 Hz, 2H), 7.16 (d, J=8 Hz, 2H), 2.44 (s, 3H), 1.58 (s, 6H). ESI-MS (M+H)+: 361.

Provenance & Evidence