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0 °C

1-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dione (15, 1.89 g, 6.54 mmol) was dissolved in 10 ml of dried DMF and cooled with an ice bath to 0° C. To the solution was added dropwise 40 ml of DMF solution containing guanidine 18 (1.369 g, 13.554 mmol). The solution was stirred at room temperature for 2 hours after addition and then further stirred at 50° C. for 24 hours. The solvent DMF was dried under vacuum and the crude product was suspended in 30 ml of chloroform. The yellow solid was collected, washed sequentially with 3×20 ml of CHCl3 and 10 ml of methanol to afford compound 4 as a white color powder (1.588 g, 6.54 mmol, 71%), mp 245° C.: NMR indicates that the compound exists in two tautomeric forms in the CDCl3 solution. 1H NMR (600 MHz, DMSO-d6) (Major tautomer): δ 8.74–8.69 (m, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.76 (d, J=2.2 Hz, 1H), 7.44 (dd, J=8.6 and 2.2 Hz), 3.73 (m, 1H), 1.14 (d, J=6.4 Hz, 6H); 13C NMR: δ 168.60, 162.45, 161.15, 161.09, 134.01, 131.84, 131.48, 131.20, 130.29, 128.86. IR: 1757, 1722, 1645, 1595, 1551, 1535, 1480, 1304, 997, 754 cm−1; MS (m/z): 342 (M+), 271, 229, 187, 127. Anal. (C13H13Cl2N5O2.0.25H2O) C, H, Cl, N.

1. additionafter addition
2. stirringfurther stirred at 50° C. for 24 hours
3. dry with materialThe solvent DMF was dried under vacuum
4. customThe yellow solid was collected
5. washwashed sequentially with 3×20 ml of CHCl3 and 10 ml of methanol