反应详情

A solution of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (1) (VII) (0.20 g, 0.57 mol) in SOCl2 (5 mL) was heated under reflux in N2 for 84 h. Excess SOCl2 was removed under reduced pressure, and the residue was chromatographed on silica gel. Elution with EtOAc/petroleum ether (3:7) gave 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzonitrile (7) (Ic: X=Cl, R=CN) (0.16 g, 87%), mp (CHCl3) 127° C. 1H NMR (CD3COCD3) δ 8.79 (s, 1 H, H-3), 8.19 (s, 1 H, H-6), 3.93 (s, 8 H, NCH2CH2Cl). 13C NMR δ 148.55 (C-5), 140.98, 139.07 (C-2,4), 129.50, 126.10 (C-3,6), 115.05 (C-1), 112.84 (CN), 54.18 (CH2N), 42.20 (CH2Cl). Anal. (C11H10Cl2N4O4) C,H,N.

1. customExcess SOCl2 was removed under reduced pressure
2. customthe residue was chromatographed on silica gel
3. washElution with EtOAc/petroleum ether (3:7)