S-methyl chlorothioformate → [(3-benzyloxy-phenyl)-(3-chloro-pyrazin-2-yl)-methyl]-thiocarbamic acid S-methyl ester

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Reaction Steps

To a suspension of C-(3-benzyloxy-phenyl)-C-(3-chloro-pyrazin-2-yl)-methylamine hydrochloride salt (3.10 g, 0.00856 mol) in dichloromethane (30 mL) were added N,N-diisopropylethylamine (2.98 mL, 0.0171 mol) and carbonochloridothioic acid S-methyl ester (946 mg, 0.00856 mol) at 0° C. After 5 min, the mixture was warmed to rt and stirred overnight. The mixture was diluted with EtOAc (100 mL), washed with water (20 mL), sat. aq. NaHCO3 (2×30 mL), brine (30 mL), and dried over anhydrous sodium sulfate. The crude product was purified by silical gel chromatogrphy (Hex: EtOAc=70:30→60:40) to give the title compound as a white solid; 1H NMR (CDCl3, 400 MHz) δ 2.34 (s, 3H), 5.03 (s, 2H), 6.53 (d, J=6.8 Hz, 1H), 6.87-6.97 (m, 3H), 7.08 (d, J=7.7 Hz, 1H), 7.22 (d, J=7.7 Hz, 1H), 7.30-7.41 (m, 5H), 8.33 (d, J=2.4 Hz, 1H), 8.51 (d, J=2.4 Hz, 1H).

Provenance & Evidence