Pyridine → HCID 178501868, compound

Participants

Reaction Steps

To a suspension of 2-methyl-2-thiopseudourea sulfate (1.50 g, 10.80 mmol) in dichloromethane (50 mL) and pyridine (1.76 mL, 21.60 mmol) at 0° C. a solution of methyl chlorooxoacetate (1.0 mL, 10.80 mmol) in dichloromethane (10.0 mL) was added and the reaction mixture was stirred for 15 hours at room temperature. Ethyl acetate (150 mL) was added into the mixture and it was washed with 1M aqueous hydrochloric acid and brine. The solvent was dried over anhydrous sodium sulfate. Filtration and concentration, followed by purification of the crude product by silica gel flash chromatography (hexane:ethyl acetate 4:3 to 3:2 eluent) gave methyl {[(1Z)-{[(methyloxy)(oxo)acetyl]amino}(methylthio)methylidene]amino}(oxo)acetate (0.87 g, 31% yield). 1H NMR (400 MHz, DMSO-d6): 12.48 (br.s, 2H), 3.81 (s, 3H), 2.41 (s, 3H); MS (EI) for C8H10N2O6S: 263 (MH+).

Provenance & Evidence