S-methyl chlorothioformate → (3-chloro-pyrazin-2-ylmethyl)-thiocarbamic acid S-methyl ester

To a suspension of C-(3-chloro-pyrazin-2-yl)-methylamine hydrochloride salt (5.13 g, 0.0285 mol) in dichloromethane (60 mL) were added N,N-diisopropylethylamine (15 mL, 0.085 mol) and carbonochloridothioic acid S-methyl ester (3.15 g, 0.0285 mol) at 0° C. After 5 min, the mixture was warmed to rt and kept at rt overnight. The mixture was diluted with dichloromethane (50 mL), washed with water (30 mL), sat. aq. NaHCO3 (2×30 mL), brine (30 mL), and dried over anhydrous sodium sulfate. The crude product was purified by silica gel chromatography (Hex:EtOAc=70:30→50:50) to give the title compound as a light-yellow solid; 1H NMR (CDCl3, 400 MHz) δ 2.41 (s, 3H), 4.76 (d, J=4.6 Hz, 2H), 6.67 (br s, 1H), 8.34 (d, J=2.5 Hz, 1H), 8.48 (d, J=2.5 Hz, 1H).

1. waitkept at rt overnight
2. washwashed with water (30 mL), sat. aq. NaHCO3 (2×30 mL), brine (30 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. customThe crude product was purified by silica gel chromatography (Hex:EtOAc=70:30→50:50)

ORD record

ord-20ced9d51c7f46f383f0aada00e8d9cd

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07648987B2