Pyridine → Ethyl 2-benzamido-4-methylthiazole-5-carboxylate

To a solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (2.00 g, 10.00 mmol) in anhydrous dichloromethane (40 mL) was added pyridine (2.50 g, 32.00 mmol), followed by the addition of benzoyl chloride (1.90 g, 13.00 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 18 h, then washed sequentially with 1 N hydrochloric acid (15 mL), saturated aqueous sodium bicarbonate (2×15 mL), and water (15 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white solid in 97% yield (3.0 g); 1H NMR (CDCl3, 300 MHz) δ 11.35 (s, br, 1H), 7.89 (d, J=7.4 Hz, 2H), 7.59 (t, J=7.4 Hz, 1H), 7.47 (t, J=7.6 Hz, 2H), 4.29 (q, J=7.1 Hz, 2H), 2.28 (s, 3H), 1.35 (t, J=7.1 Hz, 3H); MS (ES+) m/z 291.1 (M+1).

1. washwashed sequentially with 1 N hydrochloric acid (15 mL), saturated aqueous sodium bicarbonate (2×15 mL), and water (15 mL)
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationThe filtrate was concentrated in vacuo
5. customThe residue was purified by column chromatography

ORD record

ord-a688f488a9d64955b03427bc47f03263

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541457B2