Allylamine → N-Allyl-2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxamide

Participants

Reaction Steps

To a solution of 2-Bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboxylic acid (3.42 g, 9.69 mmol) in dichloromethane (59 mL) was added HOBT.H2O (1.48 g, 9.69 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.97 g, 15.5 mmol) followed by 2-propen-1-amine (2.91 mL, 38.8 mmol) and the solution was stirred at room temperature for 16 hours. The solution was then diluted with water and the layers were separated. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (3.11 g, 82%). LCMS: (AA) ES+, 393. 1H NMR (400 MHz, d1-chloroform) δ: 7.57-7.56 (m, 1H), 7.46-7.39 (m, 2H), 5.75-5.65 (m, 1H), 5.43 (br s, 1H), 5.10-5.06 (m, 1H), 5.00-4.94 (m, 1H), 3.88-3.84 (m, 2H).

Provenance & Evidence