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

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).

1. temperatureThe flask was cooled in an ice-water bath
2. additionAfter the addition
3. customthe ice water bath was removed
4. stirringthe reaction was stirred until the brown color
5. temperatureThe reaction mixture was then heated
6. temperatureat reflux for 2 hours
7. temperatureThe reaction mixture was then cooled
8. customthe solvent was evaporated
9. additionSaturated sodium bicarbonate was then added into the reaction flask
10. extractionThe resulting mixture was extracted twice with EtOAc
11. washthe combined organic layers were washed with brine
12. dry with materialdried over sodium sulfate
13. customAfter removing the solvent

ORD record

ord-b5251586743b46a3934599d6cad69348

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514566B2