1-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dione → HCID 178457568, compound

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Reaction Conditions

Reaction Steps

To the solution of the crude dione 15 (0.10 g, 0.346 mmol) in 25 ml of dry CHCl3 was added N-(benzyloxycarbonyl)-N′-isopropylguanidine (16) (0.122 g, 0.519 mmol) at room temperature. The reaction mixture was heated at 50° C. for 18 hours and then quenched with water. The mixture was extracted with chloroform and dried over Na2SO4. The CHCl3 was removed in vacuo and the crude product was recrystallized from hexanes/CHCl3 to yield compound 4d as light yellow crystals (51 mg, 0.11 mmol, 31%), mp 211° C. 1H NMR (300 MHz, CDCl3): δ 7.54–7.51(m, 2H), 7.41 (s, 5H), 7.25 (dd, J=8.6 and 2.4 Hz, 1H), 5.25 (s, 2H), 4.12 (m, 1H), 2.46 (d, J=6.6 Hz, 6H). 13C NMR: δ 170.83, 155.86, 153.87, 133.89, 132.56, 132.19, 131.22, 130.42, 129.21, 128.93, 128.65, 128.61, 125.60, 69.24, 45.25, 22.28. MS (m/z): 476 (M+), 370, 316, 314, 236. Anal. (C21H19Cl2N5O4) C, H, Cl, N.

Provenance & Evidence