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

Participants

Reaction Steps

5-(Aminomethyl)-2-chlorothiazole (1.49 g, 10.0 mmol) was dissolved in diluted hydrochloric acid (15 ml, 10.0 mmol), and O-methyl-N-nitroisourea (1.31 g, 11.0 mmol) and sodium chloride (1.17 g, 20.0 mmol) were added. pH was 2.1 at this time. This reaction mixture was adjusted to pH 6.2 with aqueous sodium hydroxide solution (0.1 N, 3.8 ml, 0.38 mmol) using pH meter. Water (1.2 ml) was added to increase the whole volume to 20 ml. After 16 hours of stirring at room temperature (pH was 6.8 at this time), the resulting white 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 1.72 g (68.6% yield) of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea.

Provenance & Evidence