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

1,3-Dibromo-propan-2-one (9 g, 42 mmol) was dissolved in methanol. (90 mL) followed by the addition of thiourea (3.2 g, 42.5 mmol) and the dark colored mixture was refluxed overnight. The solvent was then removed under reduced pressure and the remaining oil was dissolved in an ethyl acetate/water. The mixture was acidified with 1N HCl to pH 1 and extracted with three portions of ethyl acetate. The aqueous layer was then treated with solid sodium carbonate to pH 8 and again extracted with three portions of ethyl acetate. The combined, organic extracts were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product. After purification on silica gel (NH2-modified) with ethyl acetate/n-hepatane as eluents, the desired fractions were combined and concentrated under reduced pressure to yield a solid which was stirred in diethyl ether, filtered and dried to give the title compound as a light brown solid. (0.53 g, 9% yield) MS (ISP): m/e 145.1 (M−H)+

1. temperaturethe dark colored mixture was refluxed overnight
2. customThe solvent was then removed under reduced pressure
3. dissolutionthe remaining oil was dissolved in an ethyl acetate/water
4. extractionextracted with three portions of ethyl acetate
5. additionThe aqueous layer was then treated with solid sodium carbonate to pH 8
6. extractionagain extracted with three portions of ethyl acetate
7. washorganic extracts were washed with water and brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto give the crude product
12. customAfter purification on silica gel (NH2-modified) with ethyl acetate/n-hepatane as eluents
13. concentrationconcentrated under reduced pressure
14. customto yield a solid which
15. filtrationfiltered
16. customdried

ORD record

ord-b235775e79ec440ca2d4dfff006b2ee2

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07973051B2