I.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([C:11]=1[N+:12]([O-:14])=[O:13])=[N:8][Se][N:10]=2.OS([O-])=O.[Na+].[OH-].[Na+]>Cl>[Cl:2][C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[C:7]([NH2:8])[C:6]([NH2:10])=[CH:5][CH:4]=1
At room temperature, an aqueous solution of hydroiodic acid (48%, 25 ml) was added to a solution of 5-chloro-4-nitro-benzo[1,2,5]selenadiazole (8.14 g, 31.01 mmol) in concentrated aqueous hydrochloric acid (76 ml). After 2 hours at room temperature, a 5% aqueous solution of NaHSO3 (150 ml) was added, and the mixture was stirred for 15 minutes. At 0° C., concentrated aqueous NaOH solution was added until the pH value reached 8. The mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (4.98 g, 86%), which was used in the next transformation without further purification. 1H NMR (400 MHz, d6-acetone): δ=6.81 (d, J=7.7 Hz, 1H), 6.68 (d, J=7.7 Hz, 1H), 5.12 (br s, 2H), 4.78 (br s, 2H). MS (ES−): 186.2 (M−H)−.
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