4-(Chloromethyl)-N,N-dimethyl-1,3-thiazol-2-amine → (2-(Dimethylamino)thiazol-4-yl)methanol

A solution of 5.186 g (29 mmol) of 4-(chloromethyl)-2-(dimethylamino)thiazole in 100 ml of 1:1 THF/H2O was cooled to 0° C. and treated dropwise with a solution of 5.73 g (29 mmol) of silver tetrafluoroborate in 50 ml of 1:1 THF/H2O. After being stirred for 1 h, the mixture was filtered, the solid mass was washed with ethyl acetate, and the combined filtrates were concentrated in vacuo. The black residue was purified by silica gel chromatography to provide 0.80 g (17%) of the desired compound (Rf 0.24, 6% methanol in chloroform) as an oil. 1H NMR (CDCl3) δ 2.67 (br, 1 H), 3.09 (s, 6 H), 4.54 (s, 2 H), 6.35 (s, 1 H). Mass spectrum: (M+H)+ =159.

1. filtrationthe mixture was filtered
2. washthe solid mass was washed with ethyl acetate
3. concentrationthe combined filtrates were concentrated in vacuo
4. customThe black residue was purified by silica gel chromatography

ORD record

ord-1f2a640999124026a1ceb8f961214777

Source dataset

uspto-grants-1999_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05892052