Hydrochloric Acid → O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea

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Reaction Steps

5-(Aminomethyl)-2-chlorothiazole (7.43 g, 50.0 mmol) was dissolved in water (96 ml), and concentrated hydrochloric acid (4.22 ml, 50.0 mmol) was added. To this reaction mixture was added O-methyl-N-nitroisourea (6.25 g, 52.5 mmol) and chloroform (30 ml), and adjusted to pH 6.7 with aqueous sodium hydroxide solution (0.5 N) using pH meter. After 24 hours of stirring at room temperature, maintaining pH 6.7, the organic phase was separated from the water phase. The water phase was extracted with chloroform (100 ml), and the combined organic phase was concentrated under reduced. Water (50 ml) was added to the residue to stir for a while. The resulting crystals were collected by filtration under reduced pressure, and washed with water. The washed crystals were dried under reduced pressure (80° C., 2 hours) to provide 7.80 g (62.2% yield) of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea.

Provenance & Evidence