Triethylamine → 4-(Pyridin-2-yl)-1,3-thiazol-2-amine

Participants

Reaction Steps

[(2-Nitrophenyl)methyl](4-(2-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 (Example 16, Step a) (1.04 g, 4.9 mmol), 2-(bromoacetyl)pyridine hydrobromide (Aust. J. Chem. 1989, 42, 1735; 1.34 g, 4.9 mmol), and 50% MeOH (10 mL). After 2 h, the reaction was cooled to RT and the solvent was removed in vacuo. The crude material was dissolved in 50% aqueous EtOH and iron dust (Aldrich) (1.419 g, 25.2 mmol) and NH4Cl (190 mg, 3.5 mmol) was added. The reaction was heated to reflux for 1 h, then concentrated in vacuo. The residue was dissolved in THF (20 mL) and to this solution was added 4-nitrophenyl chloroformate (1.17 g, 5.8 mmol) followed by Et3N (1 mL, 7.2 mmol). The reaction was heated at reflux for 2.5 h then cooled to RT. The solvent was removed in vacuo and the crude material was purified by flash chromatography on silica gel with Hexanes:EtOAc (4:1, 1:1, 0:1) as eluant to give a tan solid. Mp: >275° C. MS m/z: 309 (M+1); 307 (M−1). Anal. Calc'd for C16H12N4OS.0.5H2O: C, 60.55; H, 4.13; N, 17.65. Found: C, 60.20; H, 4.17; N, 16.92.

Provenance & Evidence