Benzoyl isocyanate → N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide

Participants

Reaction Steps

To a solution of 2-amino-4,5-dimethylthiophene-3-carbonitrile (1680 g, 11.04 mol) in 1,4-dioxane (42 L) was added benzoylisocyanate (1624 g, 11.04 mol). The reaction mixture was then stirred at room temperature under nitrogen overnight. The resulting precipitate was collected by filtration, washed with 1,4-dioxane (3×1.7 l) and heptane (3×1.7 L), and dried under vacuum overnight to give N-(3-Cyano-4,5-dimethylthiophen-2-ylcarbamoyl)benzamide as a white solid (2800 g, 84.7% yield). 1H NMR (400 MHz, DMSO-d6) δ 2.10 (s, 3H), 2.24 (s, 3H), 7.52-7.56 (m, 2H), 7.64-7.69 (m, 1H), 8.01-8.03 (m, 2H), 11.57 (brs, 1H), 12.05 (brs, 1H). MS 300 (MH+).

Provenance & Evidence