Acetic Acid → [1,3]Thiazolo[4,5-b]pyrazine-2(3H)-thione
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[NH2:1][C:2]1[C:7](Cl)=[N:6][CH:5]=[CH:4][N:3]=1.O(CC)[C:10]([S-:12])=[S:11].[K+].CN1CCCC1=O.C(O)(=O)C>O>[S:12]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][N:6]=2)[NH:1][C:10]1=[S:11][NH2:1][C:2]1[C:7](Cl)=[N:6][CH:5]=[CH:4][N:3]=1.O(CC)[C:10]([S-:12])=[S:11].[K+].CN1CCCC1=O.C(O)(=O)C>O>[S:12]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][N:6]=2)[NH:1][C:10]1=[S:11]To a mixture of 2-amino-3-chloropyrazine (5 g, 38.6 mmol) and potassium ethyl xanthate (9.28 g, 57.9 mmol) was added 1-methyl-2-pyrrolidinone (68 mL) and the solution was heated (150° C., 16 h). The suspension was cooled (rt) and treated with glacial acetic acid (10 mL) and H2O (1500 mL). The suspension was filtered and the resulting solid was suspended and sonicated in ethanol:H2O (1:1, 500 mL). The suspension was filtered and the solid was washed with H2O, dried (calcium sulfate) in vacuo to yield the title compound as a solid (4.36 g, 67%). MS (ESI): mass calculated for C5H3N3S2, 168.98; m/z found, 170.00 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 14.69 (s, 1H), 8.42 (d, J=2.8, 1H), 8.39 (d, J=2.8, 1H).
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