Phenethyl isocyanate → 4-Oxo-3-phenethyl-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

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Reaction Steps

Phenethyl isocyanate (0.441 g, 3 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.274 g, 2 mmol) in dry dimethylsulfoxide (2.5 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by the addition of ice and the solid product (pale pink) was removed by filtration, washed with water and ethyl acetate, and recrystallised from chloroform to give the title compound. Yield: 0.259 g, 46%. IR vmax/cm−1 3132, 1743, 1668. 1H NMR δH (DMSO-d6) 3.14 (2H, t, J 7.4, CH2), 4.53 (2H, t, J 7.4, CH2), 7.21-7.33 (5H, m, ArH), 7.68 (1H, br s, NH), 7.81 (1H, br s, NH), 8.83 (1H, s, 6-H). δC 31.1, 34.6, 50.4, 127.1, 129.0, 129.2, 129.3, 131.2, 134.7, 138.2, 139.4, 162.0. MS Found 285.1161. Calc for (M+H): 285.1100. Found C, 55.0; H, 4.3; N, 29.4. Calc. for C13H12N6O3C 54.9; H 4.3; N, 29.6%.

Provenance & Evidence