Pivalic acid → HCID 18957771, compound

Participants

Reaction Steps

To a mixture of trimethylacetic acid (5.55 g, 54 mmol), 3-nitrobenzenesulphonamide (11 g, 54 mmol) and 4-dimethylaminopyridine (6.65 g, 54 mmol) in anhydrous dichloromethane (400 ml), under an atmosphere of nitrogen, was added 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (10.43 g, 54 mmol). The mixture was stirred at ambient temperature for 24 h. The mixture was extracted with 1M NaOH (50 ml) and the separated aqueous phase was mixed with dichloromethane (200 ml) and acidified with 5M HCl. The two layers were separated and the aqueous phase was further extracted with dichloromethane (2×100 ml). The combined organic phases were dried (Na2SO4) and evaporated to dryness. The resultant solid was recrystallised from methanol to afford the title compound (9 g, 58%) as a colourless solid. mp 178°-81° C. 1H NMR (360 MHz, D6-DMSO) δ 1.07 (9H, s), 7.95 (1H, t, J=8.0 Hz), 8.30-8.34 (1H, m), 8.52-8.56 (1H, m), 8.57-8.60 (1H, m), 12.02 (1H, brs).

Provenance & Evidence