Ethoxalyl chloride → HCID 10286073, compound

Participants

Reaction Steps

Ethyl chlorooxoacetate (16.3 g; 0.128 mol) was added dropwise to the solution N-(5-chloro-2-methylphenyl)-N′-methylthiourea (10.7 g; 0.05 mol) in chloroform (200 mL). The mixture was heated at reflux for 4 hours then evaporated to dryness. The residue was treated with ether (200 mL). The precipitated solid was collected by filtration and dried to give 9.7 g of 1-(5-chloro-2-methylphenyl)-3-methyl-2-thioxo-4,5-imidazolidinedione, m.p. 171–173° C. Mass spectrum; (El, M.+) m/z268/270. 1H-NMR (DMSO-d6; 300 MHz): δ 7.50–7.47 (m, 1H), 7.42–7.40 (m, 2H), 3.31 (s, 3H), and 2.15 ppm (s, 3H).

Provenance & Evidence