Isobutyric Acid → HCID 12221603, compound

Participants

Reaction Steps

To a mixture of isobutyric acid (4.6 ml, 0.05 mol), 3-nitrophenyl sulphonamide (10.1 g, 0.05 mol) and 4-dimethylaminopyridine (6.1 g, 0.05 mol) in anhydrous dichloromethane (400 ml) under an atmosphere of nitrogen was added 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (9.6 g 0.05 mol). The mixture was stirred at ambient temperature for 20 h. The mixture was extracted with 1M NaOH and tile separated aqueous phase was acidified using 5M HCl. The solid which precipitated was collected by filtration, washed with water and dried under vacuum to afford the title compound (8.16 g, 60%) as a colourless powder. mp 136°-138° C. 1H NMR (360 MHz, D6 -DMSO) δ 0.95 (6H, d, J=6.8 Hz), 2.48 (1H, septet, J=6.8 Hz), 7.95 (1H, dd, J=8.1 and 8.1 Hz), 8.33 (1H, dd, J=8.0 and 1.4 Hz), 8.54 (1H, dd, J=8.0, 1.4 Hz), 8.60 (1H, dd, J=1.4 and 1.4 Hz), 12.38 (1H, brs).

Provenance & Evidence