Ammonia → HCID 373379, compound

Participants

Reaction Conditions

Reaction Steps

The above acid (XV: X=Cl, Z=OH) was converted to the crude acid chloride (XV: X=Cl, Z=Cl), which was dissolved in dry Et2O (100 mL), cooled to 5° C., and treated dropwise with aqueous NH3 (20 mL of a 3N solution, 60 mmol). After 10 min the solution was worked up, and the residue was chromatographed on silica. Elution with EtOAc/petroleum ether (3:7) gave foreruns, while EtOAc/petroleum ether (7:3) gave 4-[N,N-bis(2-chloroethyl)amino]-3,5-dinitrobenzamide (23) (Ig: X=Cl, R=CONH2) (80% overall yield), mp (EtOAc/petroleum ether) 113°-116° C. 1H NMR (CD3COCD3) δ 8.61 (s, 2 H, H-2,6), 7.98, 7.24 (2xbr, 2 H, CONH2), 3.75 (t, J=7.0 Hz, 4 H, CH2Cl), 3.50 (t, 4 H, CH2N). 13C NMR δ 164.91 (CONH2), 149.32 (C-4), 140.07 (C-3,5), 132.18 (C-1), 128.91 (C-2,6), 56.37 (CH2N), 42.55 (CH2Cl). Anal. (C11H12Cl2N4O5) C,H,N,Cl.

Provenance & Evidence