Triethylamine → HCID 374541, compound

Participants

Reaction Steps

Reaction of this amide (XI: Z=NHCH2CH2CH2NMe2) with bis(2-chloroethyl)amine hydrochloride and Et3N as above, followed by chromatography on silica gel and elution with EtOAc/MeOH (9:1) gave N-(N,N-dimethylaminoethyl) 2-[N,N-bis(2-chloroethyl)amino]-3,5-dinitrobenzamide (20) (Ie: R=CONHCH2CH2NMe2), mp (EtOAc/petroleum ether) 115°-118° C. 1H NMR (CDCl3) δ8.63 (s, 2H, ArH4), 7.41 (br, 1H, CONH), 3.74 (t, J=6.3 Hz, 4H, CH2Cl), 3.59 (t, J=5.8 Hz, 2H, CONHCH2), 3.55 (t, J=6.3 Hz, 4H, NCH2CH2 Cl), 2.56 (t, J=5.8 Hz, 2H, CH2NMe2), 2.27 (s, 6H, NMe2). 13C NMR 164.70 (CO), 145.93 (C-2), 144.86. 141.94 (C-3,5), 135.68 (C-1), 129.63 (C4), 123.16 (C-6), 57.51 (CONHCH2), 54.82 (NCH2 CH2Cl), 45.12 (NMe2), 41.39 (NCH2CH2Cl), 37.67 (CONHCH2). Anal. (C15H21Cl2N5O5) C,H,N,Cl. (The hydrochloride salt was too hygroscopic to handle).

Provenance & Evidence