1-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dione → HCID 178512082, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of the crude dione 15 (0.551 g, 1.907 mmol) in 25 ml of dry CHCl3 was added N-(3,4-dichlorophenyl)guanidine (14) (0.389 g, 1.907 mmol) at room temperature. The reaction mixture was heated at 50° C. overnight. The solid was collected and washed sequentially with CHCl3 and H2O to afford the compound 19 as a light yellow solid (0.573 g, 1.288 mmol, 68%), mp 220° C. 1H NMR (300 MHz, DMSO-d6): δ 7.75(d, J=8.3 Hz, 1H), 7.69 (s, 1H), 7.55–7.40 (m, 3H), 7.15 (d, 7.9 Hz, 1H); 13C NMR: δ 170.54, 169.33, 160.26, 156.74, 136.75, 132.72, 131.15, 131.00, 130.73, 130.52, 129.64, 128.04. MS (m/z) 444 (MH+), 256, 227, 185. Anal. (C16H9Cl4N5O2) C, H, Cl, N.

Provenance & Evidence