2-Cyanoethanethioamide → (2'-Amino-4'-methyl-4,5'-bi-1,3-thiazol-2-yl)acetonitrile

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Reaction Steps

1-(2-Amino-4-methyl-1,3-thiazol-5-yl)-2-bromo ethanone, hydrobromide salt (Intermediate 2) (116.97 mg; 0.50 mmol; 1 eq.) and 2-cyanothioacetamide (Aldrich) (50.1 mg; 0.50 mmol; 1 eq.) are dissolved in EtOH (5 ml). The mixture is stirred at rt overnight. Solvents are evaporated, affording a yellow-orange solid which is purified by flash chromatography (CHCl3/EtOH gradient, from 50:1 to 10:1). (2′-amino-4′-methyl-4,5′-bi-1,3-thiazol-2-yl)acetonitrile is isolated as an orange solid. (71.6 mg; 61%). 1H NMR (DMSO-d6, 300 MHz) δ 2.41 (s, 3H), 4.62 (s, 2H), 7.87 (s, 1H), 9.23 (br s, 2H). M− (ESI): 235.04; M+ (ESI): 237.06. HPLC (method A), Rt: 1.16 min (purity: 98.3%).

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