65% |
With caesium carbonate; In toluene; at 100℃; for 48h;Inert atmosphere; |
To a stirred solution of 500 mg (2065 mmol) 1-chloro-9,10-anthraquinone and 1 g 3,3'-((oxybis(ethane-2,1-diyl))bis(oxy))bis(propan-1-amine) (4.544 mmol) in 40 ml of toluene was added 1480 g of cesium carbonate (4544 mmol). The reaction mixture was stirred at 100 C for 48 h until the reaction was completed. The solvent was evaporated and filtered. The residue was dissolved in dichloromethane (250 ml) and washed with water (2 x 100). The organic phase was dried over sodium sulfate and evaporated. The crude was finally purified by flash chromatography mixture of dichloromethane and methanol (90:10) obtaining of 572 mg desired compound with yield 65%. TLC (SiO2): CH2Cl2: MeOH (5:0.2); Rf = 0.20. MALDI - TOF MS: m/z 427.4 [M+H]+; (MW = 426.5). IR (neat) (cm-1): 3070, 2927, 1666, 1630, 1593, 1510, 1271,1069, 870, 806, 736. 1H NMR (CDCl3): delta (ppm): 1.97-2.03 (p, 4H, N-CH2-CH2-CH2-O, J1 = J2 = J3 = J4 = 6.4 Hz); 3.41-3.72 (m, 18H, N-CH2-CH2-CH2-O, O-CH2-CH2-O); 7.05-7.07 (dd, 1H, H2-Ar, J1 = 1.6 HzJ1 = 8.4 Hz); 7.47-7.49 (d, 1H, H4-Ar, J1 = 7.2 Hz,); 7.50-7.55 (dt,2H, H3-Ar, H6-Ar, J1 = 1.2 Hz, J1 = 1.6 Hz, J2 = 6.6 Hz, J2 = 7.4 Hz,J3 = 7.0 Hz); 7.64-7.68 (dt, 2H, H3-Ar, H6-Ar, J1 = 1.2 Hz,J2 = 7.6 Hz, J2 = 7.2 Hz, J3 = 7.4 Hz); 8.17-8.19 (dd, 1H, H5-Ar,J1 = 1.2 Hz, J1 = 1.6 Hz, J2 = 7.8 Hz);8.21-8.24 (dd, 1H, H7-Ar, J1 = 1.6 Hz, J2 = 7.6 Hz). |