N-Benzylethylenediamine → 2-Benzyl-1,2,5-thiadiazolidine 1,1-dioxide

Participants

Reaction Steps

To a refluxing solution of sulfamide (27.12 g, 282 mmol) in anhydrous pyridine (250 ml) was added dropwise N-benzylethylenediamine (42.4 ml, 282 mmol) over 3 hours. The resulting solution was refluxed under nitrogen for a further 16 hours before the solvent was removed under vacuum. The residue was dissolved in dichloromethane (100 ml) and washed with 2N hydrochloric acid (1×100 ml). The aqueous layer was extracted with dichloromethane (2×100 ml) and the combined organic solutions were washed with brine (50 ml), dried (Na2SO4) and concentrated. Flash chromatography of the residue (silica gel, dichloromethane-methanol 95:5) gave 47.3 g (79%) of the title compound as a white solid; δH (360 MHz, CDCl3) 7.32 (5H, m, Ph), 4.34 (1H, br s, --NH--), 4.18 (2H, s, Ar--CH2N--), 3.47 (2H, q, J= 6.4 Hz,--CH2NH--),3.27(2H, t, J=6.4 Hz,--CH2 --); m/z (CI) 213 (M+ +1).

Provenance & Evidence