Cyanamide → Methyl 4-amino-2-benzamidothiazole-5-carboxylate

To a solution of benzoyl isothiocyanate (4.00 mL, 29.70 mmol) and cyanamide (1.37 g, 32.50 mmol) in tetrahydrofuran (80 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (4.90 mL, 32.80 mmol) at 0° C. The resulting reaction mixture was stirred at ambient temperature for 3 hours. Methyl bromoacetate (3.00 mL, 32.00 mmol) was added to the reaction mixture. The reaction mixture was kept stirring for 1 hour at ambient temperature. Another portion of 1,8-diazabicyclo[5.4.0]undec-7-ene (4.90 mL, 32.80 mmol) was added. The reaction mixture was stirred at ambient temperature for another 16 hours. The solvent was removed in vacuo, and the residue was dissolved in ethyl acetate (200 mL), washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography to give methyl 4-amino-2-benzamidothiazole-5-carboxylate (0.16 g, 2%); 1H NMR (CDCl3, 300 MHz) δ 7.60-7.41 (m, 5H), 5.43 (s, 2H), 3.95 (s, 3H); MS (ES+) m/z 277.3 (M+1).

1. customThe resulting reaction mixture
2. stirringThe reaction mixture was kept stirring for 1 hour at ambient temperature
3. stirringThe reaction mixture was stirred at ambient temperature for another 16 hours
4. customThe solvent was removed in vacuo
5. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
6. washwashed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated
10. customthe residue was purified by column chromatography

ORD record

ord-3fa786e9ebbb4fb3912ca439f9bf0653

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541457B2