Hydrogen Bromide → O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea

Participants

Reaction Steps

5-(Aminomethyl)-2-chlorothiazole (7.43 g, 50.0 mmol) was dissolved in water (96 ml), and 47% hydrobromic acid (5.78 ml 50.0 mmol) was added. The pH was 3.4 at this time. To this reaction mixture was added O-methyl-N-nitroisourea. (7.19 g, 60.0 mmol) and sodium chloride (17.5 g, 0.30 mol), and adjusted to pH 6.2 with aqueous sodium hydroxide solution (0.5 N) using pH meter. After 24 hours of stirring at room temperature, 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 8.7 g (69.4% yield) of O-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-nitroisourea.

Provenance & Evidence