1-(Isocyanatomethyl)-2-methoxybenzene → 3-(2-Methoxybenzyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[CH2:5][N:6]=[C:7]=[O:8].[N+:13](=[C:15]1[N:19]=[CH:18][N:17]=[C:16]1[C:20]([NH2:22])=[O:21])=[N-:14]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[CH2:5][N:6]1[C:7](=[O:8])[N:19]2[CH:18]=[N:17][C:16]([C:20]([NH2:22])=[O:21])=[C:15]2[N:13]=[N:14]1Participants
4
Procedure
Ortho-methoxybenzyl isocyanate (Sigma Aldrich) (0.390 g, 2.4 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.274 g, 2 mmol) in dry DMSO (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 (off-white) removed by filtration, washed with water and ethyl acetate then recrystallised from chloroform/hexane. Yield: 0.343 g, 57%. IR vmax/cm−1 3460, 3094, 1728, 1683, 1589, 1454. 1H NMR δH (DMSO-d6) 5.45 (2H, s, CH2Ar), 6.91 (1H, td, J 7.5, 0.8, ArH), 7.06 (1H, d, J 7.8, ArH), 7.27 (1H, d, J 7.5, 1.4, ArH), 7.30-7.33 (1H, m, ArH), 7.69 (1H, br s, NH), 7.81 (1H, br s, NH), 8.84 (1H, s, 6-H). δC 47.9, 56.0, 111.3, 120.7, 123.7, 129.1, 129.4, 129.7, 131.4, 134.9, 139.6, 157.1, 162.0. MS Found 301.1100. Calc for (M+H): 301.1049. Found C, 51.6; H, 3.9; N, 28.0. Calc. for C13H12N6O3C, 52.0; H, 4.0; N, 28.0%.