[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[NH:3][C:2]1=S.C(Cl)[Cl:12].S(Cl)(Cl)(=O)=O.[OH-].[Na+]>O>[Cl:12][C:2]1[S:1][C:9]2[C:4]([N:3]=1)=[N:5][CH:6]=[CH:7][N:8]=2
A mixture of 3H-thiazolo[4,5-b]pyrazine-2-thione (4.36 g, 25.8 mmol) and DCM (60 mL) was sonicated (5 min). The suspension was treated with sulfuryl chloride (99.9 g, 740 mmol, 60 mL) and heated (40° C., 16 h). The reaction mixture was cooled (0° C.) and slowly treated with H2O (250 mL), followed by 4 N NaOH (550 mL). The aqueous mixture was extracted with EtOAc (2×1800 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as a solid (2.63 g, 53%). MS (ESI): mass calculated for C5H2ClN3S, 170.9; m/z found, 172.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 8.84 (d, J=2.5, 1H), 8.75 (d, J=2.5, 1H).
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