Pyridine → Ethyl 2-(hydrazinecarboxamido)-4-methylthiazole-5-carboxylate

Participants

Reaction Steps

To a solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (0.50 g, 2.68 mmol) and pyridine (0.32 mL, 4.03 mmol) in tetrahydrofuran (25 mL) and dichloromethane (25 mL) was added 4-nitrophenyl chloroformate (0.65 g, 3.22 mmol) at 0° C. The resulting reaction mixture was stirred at ambient temperature for 1 hour, followed by the addition of hydrazine monohydrate (3.00 mL, 59.9 mmol). The reaction mixture was stirred at ambient temperature for 18 hours and quenched with water (100 mL). The solid precipitated was filtered, washed with water and ethyl acetate and dried to afford the title compound in 78% yield (0.51 g): MS (ES+) m/z 245.2 (M+1).

Provenance & Evidence