Methoxyacetone → 4-(Methoxymethyl)-1,3-thiazol-2-amine

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Reaction Steps

1-Methoxypropan-2-one (40 g, 454 mmol) was dissolved in 300 mL of anhydrous MeOH in a 1 L round bottom flask. The flask was cooled in an ice-water bath. Br2 (73 g, 454 mmol) was added to the flask dropwise through an addition funnel. After the addition, an additional 50 mL MeOH was added to the mixture. After stirring for 20 minutes, the ice water bath was removed and the reaction was stirred until the brown color disappeared. Thiourea (34.6 g, 454 mmol) was then added into the flask. The reaction mixture was then heated at reflux for 2 hours. The reaction mixture was then cooled and the solvent was evaporated. Saturated sodium bicarbonate was then added into the reaction flask. The resulting mixture was extracted twice with EtOAc, and the combined organic layers were washed with brine and dried over sodium sulfate. After removing the solvent, the crude 4-(methoxymethyl)thiazol-2-amine was obtained. LCMS (API-ES) m/z (%) 145.2 (100%, M++H).

Provenance & Evidence