p-Toluenesulfonic acid monohydrate → HCID 22923249, compound

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Reaction Steps

A solution of N-[[(4-trifluoromethyl-2-thiazolyl)amino]thioxomethyl]-DL-phenylalanine methyl ester (2.09 g, 5.38 mmol) and p-toluene sulfonic acid hydrate (0.20 g 1.05 mmol) in toluene (80 mL) was refluxed with a Dean-Stark trap for 48 h. The reaction was cooled to room temperature, solvent removed under reduced pressure, residue taken up in ethyl acetate, washed with saturated sodium bicarbonate and saturated sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting product was recrystallized from ethyl ether-hexanes to provide 1.01 g (53%) of the titled product: mp 187°-189° C.; IR (CHCl3, cm-1) 3431, 3008, 1782, 1495, 1369, 1328, 1242, 1178, 1149, 1085; 1H NMR (300 MHz, DMSO-d6) δ 11.02 (s, 1H), 8.59 (s, 1H), 7.22-7.80 (m, 3H), 7.20-7.22 (m, 2H), 4.83 (t, 1H), 3.17 (d, 2H); MS (FD) m/e 357 (M+); UV (EtOH) 263 nm (ε=13898), 202 nm (ε=19355). Anal. Calcd. for C14H10F3N3OS2 : C, 47.05; H,2.82; N,11.76. Found: C,47.33; H, 2.86; N, 11.67.

Provenance & Evidence