Thiazole → bromothiazole N-(4-bromophenyl)-N-(4-ethyl-1,3-thiazol-2-yl)amine

Participants

Reaction Steps

Procedure for thiazole synthesis: 9H-9-fluorenyl-methyl-N-[(4-bromoanilino)carbothioyl]carbamate (0.25 g, 0.55 mmol) was dissolved in piperidine/N,N-dimethylformamide (1:6, 3.5 mL) and the mixture stirred at ambient temperature for 2 h. The solvent was removed under reduced pressure and the residue dissolved in a mixture of acetic acid (1 mL), ethanol (2 mL), and dioxane (2 mL). 1-Bromo-2-butanone (90%, 0.11 mL, 1.10 mmol) was added and the mixture was stirred for 14 h at ambient temperature. The reaction mixture was diluted with half saturated aqueous sodium carbonate (15 mL) and extracted with methanol/dichloromethane (1:19, 3×20 mL). The combined organic layers were dried (magnesium sulfate), filtered, concentrated and purified by flash column chromatography on silica gel using ethyl acetate/heptane (1:4) to afford the bromothiazole N-(4-bromophenyl)-N-(4-ethyl-1,3-thiazol-2-yl)amine (0.15 g, 0.53 mmol): RP-HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a 5μ Hypersil HS C18, 250×4.6 mm column) Rt 13.15 min.

Provenance & Evidence