Ethyl [(5-nitro-1,3-thiazol-2-yl)amino](oxo)acetate synthesis

Yield:89792-36-9 90%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 6 h;

Steps:

4 Synthesis of ethyl [(5-nitro-1,3-thiazol-2-yl)amino](oxo)acetate (14)

To a solution of 2-amino-5-nitro-1,3-thiazole (0.0015 mol) in dichloromethane, was added triethylamine (1.2 equiv). The reaction mixture was stirred at 5 °C for 15 min. After that, a solution of ethyl chlorooxoacetate (0.0018 mol, 1.2 equiv) was added droopingly. The reaction mixture was stirred at room temperature for 6 h. After complete conversion as indicated by TLC, the solvent was removed in vacuo, the residue was neutralized with saturated NaHCO₃ solution, and the aqueous layer was extracted with ethyl acetate (3 x 15 mL), washed with water (3 * 20 mL), and dried over anhydrous Na₂SO₄. The solvent was evaporated in vacuo and the precipitated solids were recrystallized from a mixture of acetonitrile/methanol. Yield: 90%, mp: 252-255 °C. ¹H NMR (400 MHz, DMSO-d₆) δ: 8.67 (1H, s, H-4), 4.32 (2H, q, O-CH₂) 1.31 (3H, t, CH₃) ppm; ¹³C NMR (100 MHz, DMSO-d₆) δ: 161.7 (C-2), 158.4 (CO-OR), 157.7 (RNH-CO), 143.3 (C-5), 142.7 (C-4), 63.4 (O-CH₂), 14.1 (CH₃) ppm; MS (FAB⁺) m/z 246 (M+H⁺). Anal. Calcd for C₇H₇N₃O₅S: C, 34.29; H, 2.88; N, 17.14. Found: C, 34.19; H, 2.83; N, 17.09.

References:

Nava-Zuazo, Carlos;Chávez-Silva, Fabiola;Moo-Puc, Rosa;Chan-Bacab, Manuel Jesús;Ortega-Morales, Benjamín Otto;Moreno-Díaz, Hermenegilda;Díaz-Couti?o, Daniel;Hernández-Nú?ez, Emanuel;Navarrete-Vázquez, Gabriel [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 5,p. 1626 - 1633]