ChemicalBook CAS DataBase List 4-(6-Methoxybenzo[d]thiazol-2-yl)-N,N-dimethylaniline

4-(6-Methoxybenzo[d]thiazol-2-yl)-N,N-dimethylaniline synthesis

11synthesis methods

Product Name:4-(6-Methoxybenzo[d]thiazol-2-yl)-N,N-dimethylaniline
CAS Number:10205-71-7
Molecular formula:C16H16N2OS
Molecular Weight:284.38

43036-17-5

74-88-4

4-(6-Methoxybenzo[d]thiazol-2-yl)-N,N-dimethylaniline

10205-71-7

401813-34-1

6-methoxy-2-(4-aminophenyl)benzothiazole (6) (15 mg, 0.059 mmol), methyl iodide (MeI) (8.3 mg, 0.060 mmol) and potassium carbonate (K2CO3) (100 mg, 0.72 mmol) were reacted in anhydrous dimethylsulfoxide (DMSO) (0.5 ml) at 100 °C for 16 hours. The reaction mixture was purified by reversed-phase thin layer chromatography (TLC) (methanol:water=7:1) to afford 6-methoxy-2-(4-methylaminophenyl)benzothiazole (7) (2.0 mg, 13.3%) and 6-methoxy-2-(4-dimethylaminophenyl)benzothiazole (8) (6 mg, 40%). 1H NMR (300MHz, acetone-d6) δ of compound 7: 7.85 (d, J=8.7Hz, 2H, H-2',6'), 7.75 (dd, J=8.8Hz, J=1.3Hz, 1H, H-4), 7.49 (d, J=2.4Hz, 1H, H-7), 7.01 (dd, J=8.8Hz, J=2.4 Hz, 1H, H-5), 6.78 (d, J=7.6 Hz, 2H, H-3',5'), 3.84 (s, 3H, OMe), 2.91 (s, 3H, NMe). 1H NMR (300MHz, acetone-d6) δ of compound 8: 7.85 (d, J=8.7Hz, 2H, H-2',6'), 7.75 (dd, J=8.8Hz, J=1.3Hz, 1H, H-4), 7.49 (d, J=2.4Hz, 1H, H-7), 7.01 (dd, J=8.8Hz, J=2.4 Hz, 1H, H-5), 6.78 (d, J=7.6 Hz, 2H, H-3',5'), 3.84 (s, 3H, OMe), 3.01 (s, 6H, NMe2). Using the same strategy, other 2-(4'-aminophenyl)benzothiazole derivatives can be synthesized by selecting appropriate substituted aniline derivatives (e.g., 2-, 3- or 4-methylaniline) and appropriate 4-nitrobenzoyl chloride derivatives (e.g., 2- or 3-methyl-4-nitrobenzoyl chloride).