Water → 4-(1,1-Dioxo-5-methyl-1,2,5-thiadiazolidine-2-yl)nitrobenzene

Participants

Reaction Steps

To a solution of 2-methyl-1,2,5-thiadiazolidine-1,1-dioxide (2.02 g, 14.8 mmol) in anhydrous dimethylformamide (30 ml) was added sodium hydride (60% dispersion in oil; 0.59 g) and the mixture was stirred at room temperature under nitrogen for 40 minutes. A solution of 1-fluoro-4-nitrobenzene (2.09 g, 14.8 mmol) in anhydrous dimethylformamide (15 ml) was added to the above solution and the mixture was refluxed for 1 hour. Water (200 ml) was added and products were extracted with ethyl acetate (2×150 ml), dried (MgSO4) and concentrated to an orange solid. Crystallisation from ethyl acetate (150 ml) afforded 2.61 g (68.7%) of the title compound as a pale orange solid; mp 155°-163° C.; δH (250 MHz, DMSO-d6) 8.29 (2H, d, J=9.3 Hz, Ar--H), 7.34 (2H, d, J=9.3 Hz, Ar--H), 4.00 (2H, t, J=6.4 Hz, --CH2 --), 3.57 (2H, t, J=6.4 Hz, --CH2 --), 2.78 (3H, s, --CH3); m/z (EI) 257 (M+).

Provenance & Evidence