3-Chloro-1-propanol → 3-((4-Fluorophenyl)(thiazol-2-yl)amino)propan-1-ol

Participants

Reaction Steps

A mixture of N-(4-fluorophenyl)thiazol-2-amine (6.00 g, 30.0 mmol), 3-chloropropanol (3.87 mL, 46.4 mmol), tetra-n-butylammonium hydrogensulfate (1.05 g, 3.09 mmol) in toluene (100 mL) and NaOH (40% w/v in water)(20 mL) was refluxed for 3 h. On cooling, the reaction mixture was diluted with EtOAc (100 mL), washed with water (4×100 mL), brine (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography with 50-80% EtOAc in hexane to afford the title compound as a brown oil, 3.287 g. MS (M+H)+ 253.

Provenance & Evidence