Synthesis of Sulfathiazole at Mild Conditions

Document Type : Research Note


Applied Chemistry Research Group, ACECR-University of Tehran Branch, P.O. Box 13145-186 Tehran, I.R. IRAN


Sulfathiazole, a sulfa drug with molecular formula C9H9N3O2S2, known as antibacterial agent in pharmaceutical industries and used for treatment of bacterial infections in human beings and veterinary in wide range. Many synthetic methods for synthesis of sulfathiazole are reported, but these reactions involves use of expensive and toxic solvents with low yields. Herein, we use different solvents to make sulfonamide group in sulfathiazole synthesis method. Among them the best results obtained in 2-Picoline as an efficient, inexpensive, and economically viable solvent with good yields.  


Main Subjects

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[15] Selected Spectra Data: Acetylsulfathiazole (C), C11H11N3O3S2, MW: 297.35, mp: 250-254°C, IR n(cm-1): 630(C-S), 1089, 1147(-SO2NH-), 1301 (S=O), 1500 (C=C), 1525(C-S), 1591 (C=N), 1672(CONH), 3107, 3292(NH), 1H NMR(DMSO-d6) d(ppm): 2.08(s, 3H), 6.61(d, 2H, J=9.05Hz) 6.79(d, 1H, J=4.56 Hz), 7.21(d, 1H, J=4.58 Hz), 7.72(d, 2H, J=9.10 Hz), 10.2(s, 1H), 12.6(bs, 1H), Sulfathiazole(D), C9H9N3O2S2, MW: 255.3, mp: 201-202 °C, IR n(cm-1): 626 (C-S), 1087, 1141(-SO2NH-), 1267(S=O), 1325, 1500(C=C), 1529(C-S), 1596(C=N), 3234, 3320(NH), 1H NMR (DMSO-d6) d(ppm): 5.77(bs, 2H), 6.57(d, 2H, J=8.66 Hz), 6.73(d, 1H, J=4.6 Hz), 7.16 (d, 1H, J=4.6 Hz), 7.44(d, 2H, J=8.64 Hz), 12.34(bs, 1H)