Triethylamine → 4-(3-Pyridinyl)-2-thiazolamine

Participants

Reaction Steps

[(2-Nitrophenyl)methyl](4-(3-pyridyl)(1,3-thiazol-2-yl)amine was prepared according to the method described in Example 16 (Step b) by employing amino{[(2-nitrophenyl)methyl]amino}methane-1-thione (1.03 g, 4.9 mmol) (Example 16, Step a), 3-(bromoacetyl)pyridine hydrobromide (Aust. J. Chem. 1989, 42, 1735; 1.37 g, 4.9 mmol), and 50% MeOH (50 mL). The crude yellow oil, iron dust (Aldrich) (1.39 g, 24.9 mmol) and NH4Cl (198 mg, 3.7 mmol) in 50% EtOH (50 mL) was heated at reflux. After 1 h the solvent was removed in vacuo. The residue was dissolved in THF (20 mL) and to this solution was added 4-nitrophenyl chloroformate (Aldrich) (860 mg, 4.2 mmol) followed by Et3N (0.85 mL, 6.1 mmol) and the reaction was heated at reflux. After 1 h the reaction was cooled to RT and stirred overnight. The solvent was removed in vacuo and purified by flash chromatography on silica gel with Hexanes:EtOAc (1:1) to CH2Cl2:MeOH (39:1, 19:1) as eluant to give an off-white solid. Mp: 269–272° C. MS m/z: 309 (M+1). Calc'd for C16H12N4OS—308.07.

Provenance & Evidence