2-Chloro-3,5-dinitrobenzoic acid → HCID 12897330, compound

Participants

Reaction Steps

Reaction of commercially-available 2-chloro-3,5-dinitrobenzoic acid (X) with SOCl2 gave 2-chloro-3,5-dinitrobenzoyl chloride (XI: Z=Cl), which was quenched with ammonia to give 2-chloro-3,5-dinitrobenzamide (XI: Z=NH2). A solution of this amide (1.00 g, 4.07 mmol) and Et3N (1.42 g, 10 mmol) in p-dioxane (30 mL) was treated with N,N-bis(2-chloroethyl)amine hydrochloride (1.45 g, 8.14 mmol) at 50° C. for 18 h. The mixture was then poured into water and extracted with EtOAc to give an oil, which was chromatographed on silica gel. Elution with EtOAc/petroleum ether (1:1) gave 2-[N,N-bis(2-chloroethyl)amino]-3,5-dinitrobenzamide (19) (Ie: R=CONH2) (1.15 g, 80%), mp (CHCl3 /petroleum ether) 123°-124° C. 1H NMR (CH3SOCD3) δ 8.70 (d, J=2.7 Hz, 1 H, H-4), 8.49 (d, J=2.7 Hz, 1 H, H-6), 7.68, 7.35 (2xbr, 2H, CONH2), 3.80, 3.61 (2xt, J=6.9 Hz, 8 H, NCH2CH2Cl). 13C NMR δ 167.94 (CONH2), 147.27 (C-2), 147.20, 142.84 (C-3,5), 137.70 (C-1), 128.40, 123.24 (C-4,6), 55.84 (CH2N), 42.28 (CH2Cl). Anal. (C11H12Cl2N4O5) C,H,N,Cl.

Provenance & Evidence