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

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of N-benzylethylenediamine (2.000 g, 13.3 mmol) in pyridine (20 mL) was added sulfamide (1.919 g, 20.0 mmol). The mixture was heated in an oil bath at 120° C. for 16 hrs. After cooling to room temperature, the mixture was concentrated and the residue was partitioned between ethyl acetate and saturated aqueous sodium chloride. The organic layer was washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated. The residue was purified by silica gel chromatography (0-80% ethyl acetate/hexanes) to afford the product as a light yellow thick oil (1.4 g, 50%). 1H NMR (300 MHz, CDCl3) δ 7.40-7.30 (m, 5H), 4.38 (br s, 1H), 4.20 (s, 2H), 3.50 (q, 2H, J=6.6 Hz), 3.29 (t, 2H, J=6.6 Hz).

Provenance & Evidence