Hydrazine → 2-Aminomethyl-3-methylimidazo[5,1-b]thiazole

Participants

Reaction Steps

A 0.052 ml portion of anhydrous hydrazine was added to 15 ml of a dry methanol solution containing 380 mg of 2-phthalimidomethyl-3-methylimidazo[5,1-b]thiazole, followed by heating under reflux for 6 hours. The reaction solution was cooled on ice, and the resulting crystal was filtered and then washed with a small amount of cold methanol. The filtrate was concentrated under reduced pressure, and to the resulting residue, 15 ml of dichloromethane was added. Afterward, the solution was extracted with 15 ml of 2N hydrochloric acid, and the hydrochloric acid extract was alkalified with potassium hydroxide. The organic layer extracted from the aqueous layer with dichloromethane (40 ml×3) was dried over anhydrous potassium carbonate, followed by filtration. The solvent was then evaporated under reduced pressure to obtain 185 mg of 2-aminomethyl-3-methylimidazo[5,1-b]thiazole as a milky white powder.

Provenance & Evidence