2-Chloro-N-(4-fluoro-2-phenylaminophenyl)acetamide → 2-(chloromethyl)-6-fluoro-1-phenyl-1H-1,3-benzodiazole

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Reaction Conditions

Reaction Steps

2-Chloro-N-(4-fluoro-2-phenylaminophenyl)acetamide (740 mg, 2.62 mmol) was dissolved in AcOH (20 mL) and the mixture heated at 70° C. under a nitrogen atmosphere for 5 h. The volatiles were removed in vacuo and the resulting residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous phase was extracted with DCM (×3). The combined organic fractions were washed with water, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-5% MeOH in DCM) to afford the title compound as a brown oil which crystallised on standing (570 mg, 84%). LCMS (Method C): RT 3.40 min [M+H]+ 261.2. 1H NMR (CDCl3, 400 MHz): δ 7.75 (1H, dd, J=8.87, 4.76 Hz), 7.66-7.54 (3H, m), 7.47 (2H, d, J=7.38 Hz), 7.07 (1H, td, J=9.21, 2.41 Hz), 6.84 (1H, dd, J=8.54, 2.41 Hz), 4.66 (2H, s). 1

Provenance & Evidence