Urea → HCID 54101854, compound

Participants

Reaction Steps

To a stirred slurry of 16.8 g. (0.1 mol) of N-(2-fluorophenyl)-N'-methyl urea, dissolved in 500 ml. of acetone containing 9.24 g. (0.11 mol) of sodium bicarbonate was added 10.6 g. ((0.11 mol) of chloromethyl methyl sulfide. The resulting mixture was stirred for 2 hours at a gentle reflux. The precipitated solid was removed by filtration. The filtrate was evaporated to give a clear oil. Crystallization from benzene gave 7.1 g. of the original urea. The filtrate from this crystallization was evaporated and the residue crystallized from diethylether to give 3.4 g. of a crystalline solid product, melting point 81°-82°C. Analysis calculated for C10H13FN2OS: S, 14.03%; F, 8.32%. Found: S, 14.02%; F, 8.43%. The infrared spectrum showed strong adsorption at 3.0, 6.9, 7.3 and 13.0μ. The NMR spectra was consistent with the assigned structure.

Provenance & Evidence