2-Chloroethyl isocyanate → HCID 18789690, compound

Participants

Reaction Steps

To a mixture of N-(3-amino-2-methyl-phenyl)-methanesulfonamide (1.5 g, from Example 6, part 1) in THF (30 mL) was added 2-chloroethylisocyanate (0.7 mL) dropwise at 0° C. The reaction mixture was slowly warmed to room temperature and stirred overnight. The precipitate was filtered, rinsed with THF, and dried to give N-{3-[3-(2-chloro-ethyl)-ureido]-2-methyl-phenyl}-methanesulfonamide (1.8 g). To the above compound (1.7 g) in acetonitrile (100 mL) was added potassium fluoride (40 wt. % on alumina) (3.5 g). The mixture was heated at 80° C. for 8 hr and filtered, washed with methanol . The filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with methanol:dichloromethane (5:95) to afford N-[2-methyl-3-(oxazolidin-2-ylideneamino)-phenyl]-methanesulfonamide. This was converted to oxalate salt (0.5 g), mp 124-140° C. in a manner similar to that described above in Example 7, part 4.

Provenance & Evidence