3-Chloro-5-(thiazol-5-yl)aniline synthesis

Yield:-

Reaction Conditions:

with tin(ll) chloride in ethanol at 90; for 1.5 h;

Steps:

262

3-ChIoro-5-thiazol-5-ylphenylamine; [755] To a solution of 5-(3-chloro-5-nitrophenyl)thiazole (0.120g, 0.499mmol) inethanol (5mL) was added tin dichloride (0.9555g, 4.986mmol). The mixture was stirred at90°C for 1.5h. After cooling to rt, sat. NaHC0₃ (aq) was added dropwise to adjust the pH to9-10. The resulting suspension was filtered through a Celite pad. The filtrate wasconcentrated to dryness in vacua to afford the title compound, which was used directly in thenext step without purification. 'H-NMR (CD₃OD, 400 MHz): 5 = 6.67 (t, J= 2.0 Hz, 1 H),6.85 (t, J= 1.6 Hz, 1 H), 6.88 (t, J= 1.6 Hz, 1 H), 8.10 (s, 1 H), 8.94 (s, 1 H). MS (ES+): m/z211.10 (MH+, ³⁵C1), 213.12 (MH⁺, ³⁷C1). HPLC: t_R = 2.92 min (ZQ2000, polar_5min).

References:

WO2006/17443,2006,A2 Location in patent:Page/Page column 166-167