Thionyl Chloride → HCID 10339159, compound

Participants

Reaction Steps

Treatment of (6) with excess SOCl2 containing a drop of DMF under reflux for 20 min, followed by concentration to dryness and azeotroping with benzene, gave crude 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzoyl chloride (VI: X=Cl; Y1 =Cl). This was dissolved in Me2CO (20 mL), cooled to 0° C., treated with excess 40% aqueous methylamine. The product was purified by chromatography on silica gel, elution with EtOAc/petroleum ether (1:1) giving N-methyl [N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (8) (Ib: X=Cl, R=CONHMe), mp (EtOAc/petroleum ether) 180.5° C. 1H NMR (CD3COCD3) δ 8.53 (s, 1 H, ArH3), 7.75 (br, 1 H, CONH), 7.56 (s, 1 H, H-6), 3.88-3.80 (m, 8 H, NCH2CH2Cl), 2.90, 2.89 (2 s, 3 H, CONHMe). 13C NMR δ 165.89 (CONH), 148.43 (C-5), 140.05, 138.26 (C-2,4), 138.94 (C-1), 125.05, 122.45 (C-3,6), 54.20 (CH2N), 42.10 (CH2Cl), 26.69 (CONHCH3). Anal. (C12H14Cl2N4O5) C,H,N,Cl.

Provenance & Evidence