反应详情

A solution of methyl 4-chloro-3,5-dinitrobenzoate (XIV) (10.0 g, 0.036 mol) and diethanolamine (7.66 g, 0.073 mol) in ρ-dioxane (60 mL) was stirred at 50° C. for 5h. Volatiles were removed under reduced pressure, and the residue was adsorbed directly onto silica gel and chromatographed. Elution with EtOAc/petroleum ether (1:10) gave foreruns, and subsequent elution with EtOAc/petroleum ether (3:2) gave methyl 4-[N,N-bis(2-hydroxyethyl)amino]-3,5-dinitrobenzoate (XV: X=OH, Z=OMe) (9.61 g, 80%), mp (CHCl3 /petroleum ether) 101°-103° C. 1H NMR (CDCl3) δ8.52 (s, 2H, ArH-2,6), 3.97 (s, 3 H, COOCH3), 3.76 (dxt, J=6.5, 4.7 Hz, 4H, CH2OH), 3.26 (t, J=4.7 Hz, 4H, NCH2), 2.76 (t, J=6.5 Hz, 2 H, OH). 13C NMR δ163.14 (COOCH3), 145.50 (C-4), 142.54 (C-3,5), 131.19 (C-2,6), 123.59 (C-1), 59.16 (CH2OH)1, 54.58 (CH2N), 53.14 (OCH3). Anal. (Cl12H15N3O8) C,H,N.

1. customVolatiles were removed under reduced pressure
2. customchromatographed
3. washElution with EtOAc/petroleum ether (1:10)
4. customgave
5. washforeruns, and subsequent elution with EtOAc/petroleum ether (3:2)