1-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dione → HCID 178457571, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of the crude dione 15 (0.7 g, 2.5 mmol) in 25 ml of dry CHCl3 was added N-isopropyl-N′-(tert-butoxycarbonyl)-guanidine (17) (0.5 g, 2.5 mmol). The reaction mixture was heated at 50° C. for 16 hours. The reaction was quenched with water, extracted with chloroform and dried over Na2SO4. The solvent was removed in vacuo and the crude product was purified with a silica gel column and was eluted with 3% EtOAc/CHCl3 to yield 4c as a white solid (0.25 g, 22%), mp 227° C. 1H NMR (300 MHz, CDCl3): δ 7.55 (d, J=2.4 Hz, 1H), 7.53(d, J=8.6 Hz, 1H), 7.27 (dd, J=8.6 and 2.4 Hz, 1H), 4.15 (m, 1H), 1.54 (s, 9H), 1.24 (d, J=6.6 Hz, 6H); 13C NMR: δ 170.50, 168.40, 159.34, 156.09, 153.00, 132.51, 132.09, 131.34, 130.38, 128.62, 125.62, 85.59, 45.05, 29.70, 22.34. IR: 2979, 2930, 1766, 1729, 1532, 1474, 1142, 775, 734 cm−1. MS (m/z): 444 (M++1).

Provenance & Evidence