4,5-Dimethylthiazole-2-carbaldehyde oxime → (Dimethyl-1,3-thiazol-2-yl)methanamine

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Reaction Steps

The crude 4,5-dimethylthiazole-2-carbaldehyde oxime (300 mg, 2 mmol) was dissolved in acetic acid (25 mL), zinc dust (1.8 g, 27.5 mmol) was added portionwise at room temperature and the reaction mixture was stirred at room temperature for 3 hours. The mixture was then filtered over a pad of celite and rinsed with methanol. Toluene was added and the filtrate was concentrated. An aqueous solution of NH4Cl was added, the solution was acidified to pH=2 with HCl (1N) and extracted with diethyl ether and ethyl acetate. The aqueous layer was basified with aqueous NaOH to pH=10, and then extracted with diethyl ether and ethyl acetate. Combined organic extracts were dried over sodium sulfate, filtered and evaporated to give crude (4,5-dimethyl-1,3-thiazol-2-yl)methylamine as a pale yellow oil which was used in the next step without purification. LCMS m/z (M+H) 143.1 found, 143.1 required.

Provenance & Evidence