Dimethylformamide → HCID 66749706, compound

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Reaction Steps

To a solution of 2,4-dibromo-1,3-thiazole-5-carboxylic acid (25.0 g, 87.1 mmol) in dichloromethane (600 mL) at 0° C. was added thionyl chloride (66.1 mL, 906 mmol) followed by N,N-dimethylformamide (7.02 mL, 90.6 mmol). The mixture was allowed to warm to room temperature and stir for 2 hours. The solvent was evaporated and the excess thionyl chloride was removed by azeotroping with toluene. The residue was dissolved in dichloromethane (600 mL) and cooled to 0° C., then added triethylamine (63.2 mL, 453 mmol) was added followed by 2-propen-1-amine (23.8 mL, 317 mmol) and N,N-dimethylaminopyridine (1.11 g, 9.06 mmol). The mixture was allowed to warm to room temperature and stirred for 2 hours. The solution was then diluted with dichloromethane and water and the layers were separated. The aqueous phase was then extracted with dichloromethane twice, then the combined 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 (14.3 g, 50%). LCMS: (FA) ES+ , 327. 1H NMR (400 MHz, d4-methanol) δ: 5.97-5.85 (m, 1H), 5.32-5.24 (m, 1H), 5.20-5.14 (m, 1H), 4.02-3.95 (m, 2H).

Provenance & Evidence