Diethanolamine → HCID 10360491, compound

Participants

Reaction Steps

A solution of 5-chloro-2,4-dinitrobenzenesulfonamide (VIII) [Herbert, R. B. and Hollman, R. G. Tetrahedron, 1965, 21, 663-675] (1.55 g, 5.5 mmol) and diethanolamine (1.16 g, 11 mmol) in dioxan (100 mL) was held at 60° C. for 1.5 h, then adsorbed directly onto silica gel. Excess solvent was evaporated under reduced pressure, and the residue was chromatographed on silica gel, eluting with EtOAc/MeOH (19:1), to give 5-[N,N-bis(2-hydroxyethyl)amino]-2,4-dinitrobenzenesulfonamide (IX) (1.91 g, 99%), mp (EtOAc/petroleum ether) 138°-139° C. 1H NMR ((CD3)2SO) δ 8.53 (s, 1 H, H-3), 7.97 (s, 1 H, H-6), 7.93 (br s, 2 H, SO2NH2), 4.88 (t, J=5.1 Hz, 2 H, OH), 3.65 (dt, J=5.2, 5.1 Hz, 4 H, CH2OH), 3.49 (t, J=5.1 Hz, 4 H, NCH2). 13C NMR δ 146.84 (C-5), 140.53 (C-1), 136.84, 134.39 (C-2,4), 125.70 (C-3), 54.27 (NCH2). Anal. (C10H14N4O8S) C,H,N.

Provenance & Evidence