Hydrochloric Acid → Methyl 2-formyl-1,3-thiazole-4-carboxylate

Thiazole-4-carboxylate 3 (30 g, 122 mmol) was dissolved in 300 mL of acetone, to which was added aqueous HCl (21 mL, 2M). After keeping the reaction mixture at RT for overnight, the reaction mixture was heated up and kept at 60° C. for 2 h. The reaction mixture was then cooled and evaporated under vacuum to give a residue which was taken up in 200 mL of DCM. DCM solution was then washed with saturated NaHCO3 solution and then brine and dried over anhydrous Na2SO4. DCM solution was filtered and concentrated under vacuum to give the concentrated solution which was triturated by ether to give methyl 2-formylthiazole-4-carboxylate 4 (14 g, 82 mmol, 54% for two steps) as a white solid. 1HNMR (400 MHz, CDCl3) δ 133-8-p 110.16 (d, J=1.3 Hz, 1H), 8.53 (d, J=1.3 Hz, 1H), 4.01 (s, 3H).

1. customat RT
2. customfor overnight
3. temperaturethe reaction mixture was heated up
4. temperatureThe reaction mixture was then cooled
5. customevaporated under vacuum
6. customto give a residue which
7. washDCM solution was then washed with saturated NaHCO3 solution
8. dry with materialbrine and dried over anhydrous Na2SO4
9. filtrationDCM solution was filtered
10. concentrationconcentrated under vacuum
11. customto give the concentrated solution which
12. customwas triturated by ether

ORD record

ord-284fe35eb03b4ab498fce1eb525670d6

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09226974B2