Aniline → HCID 18537266, compound

Participants

Reaction Steps

Methyl 5-methylthio-4-(N-phenylcarbamoyl)thiophene-2-carboxylate: To 182 mg (0.785 mmol) of 5-(methoxycarbonyl)-2-methylthiothiophene-3-carboxylic acid (as prepared in Example 95) in 4 mL of anhyd CH2Cl2 was treated with 275 μL (3.15 mmol) of oxalyl chloride and 6 μL of anhyd DMF for 2 h similar to Example 79, step (a); followed by 206 μL (1.18 mmol) of N,N-diisopropylethylamine and 85.9 μL (0.942 mmol) of aniline in 3 mL of anhyd CH2Cl2 for 20 min. The mixture was poured into 25 mL of EtOAc and washed with 1 M HCl (2×25 mL), saturated NaHCO3 (2×25 mL), and brine (25 mL), and dried over Na2SO4. Removal of the solvent in vacuo, afforded the pure title compound as a light yellow solid (163 mg, 68%). 1H-NMR (300 MHz, CDCl3) δ 8.23 (broad s, 1H), 8.10 (s, 1H), 7.63 (d, 2H, J=7 Hz), 7.36 (t, 2H, J=7 Hz), 7.15 (t, 2H, J=7 Hz), 3.90 (s, 3H), and 2.64 (s, 3H).

Provenance & Evidence