Ethyl 2'-(acetylamino)-4'-methyl-4,5'-bi-1,3-thiazole-2-carboxylate → 2'-(Acetylamino)-N-allyl-4'-methyl-4,5'-bi-1,3-thiazole-2-carboxamide

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Reaction Conditions

Reaction Steps

In a microwave tube, ethyl 2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazole-2-carboxylate, Compound (1), (1.0 g, 3.21 mmol, 1 eq.) is dissolved in allylamine (Fluka)(6 ml). The reaction mixture is heated at 80° C. for 20 min under microwave irradiation. The reaction is complete, but some desacetylation is observed. The solvents are evaporated and the crude product is recrystallized in MeOH. Compound (2) is isolated as pale yellow solid (492.9 mg; 47%). 1H NMR (DMSO-d6, 300 MHz) δ 2.15 (s, 3H), 2.50 (s, 3H), 3.91 (m, 2H), 5.10 (d, J=12 Hz, 1H), 5.17 (d, J=18 Hz, 1H), 5.88 (m, 1H), 7.99 (s, 1H), 8.94 (t, J=5 Hz, 1H), 12.14 (br s, 1H). M− (ESI): 321.17; M+ (ESI): 323.18. HPLC (method A), Rt: 2.84 min (purity: 99.6%).

Provenance & Evidence