Oxalyl chloride → HCID 10192786, compound

Participants

Reaction Steps

Oxalyl chloride (8.4 g; 0.066 mol) was added dropwise to the stirring solution of N-(2,6-dimethyl phenyl)-N′-methylthiourea (6.4 g; 0.033 mol) in methylene chloride (100 mL). The mixture was heated at reflux for 2 hours then evaporated to dryness. Ethanol (100 mL) was added and the mixture was heated at reflux for 1 hour. The solvent was concentrated. The precipitated solid was collected by filtration and dried to give 5.4 g of 1-(2,6-Dimethylphenyl)-3-methyl-2-thioxo-4,5-imidazolidinedione, m.p. 144–146° C. Mass spectrum; (El, M.+) m/z248. 1H-NMR (DMSO-d6; 300 MHz): δ 7.30 (t, 1H), 7.18 (d, 2H), 3.33 (s, 3H), and 2.08 ppm (s, 6H).

Provenance & Evidence