Cyanoacetamide → HCID 2408012, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-cyanoacetamide (3.0 g, 36 mmol) in DMF (50 mL) was added sodium hydride (60% in mineral oil, 1.43 g, 35.7 mmol, 1 eq.), and the mixture stirred at 0° C. for 1 hour, giving a clear solution. 4-Methoxyphenyl isothiocyanate (15.90 g, 35.7 mmol, 1 eq.) in DMF (10 mL) was added, and stirred for 30 minutes, then 2-bromo-4′-chloroacetophenone (8.33 g, 35.7 mmol, 1 eq.) and potassium carbonate (4.93 g, 35.7 mmol, 1 eq.) were added, and the mixture was stirred at room temperature for 1 week. Water (200 mL) was added; and the dark precipitate that formed was filtered, washed with water (3×50 mL), ethyl acetate (3×15 mL), and acetone (3×15 mL), then dried under vacuum to give 4-amino-5-(4-chlorobenzoyl)-2-[(4-methoxyphenyl)amino]thiophene-3-carboxamide (5.6 g) as a light orange solid. 1H NMR (DMSO-d6): δ 9.97 (1H, s), 8.03 (2H, s), 7.54 (2H, d, J=8.2 Hz), 7.48 (2H, d, J=8.2 Hz), 7.41 (2H, s), 7.25 (2H, d, J=8.6 Hz), 6.94 (2H, d, J=8.6 Hz), 3.74 (3H, s).

Provenance & Evidence