p-Toluenesulfonic acid monohydrate → HCID 19704188, compound

Participants

Reaction Steps

A solution of N-[[(6-fluoro-2-benzothiazolyl)amino]thioxomethyl]-DL-phenylalanine methyl ester (0.90 g, 2.31 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 251 mg (31%) of the titled product: mp 223°-224° C.; IR (KBr, cm-1) 3173, 1767, 1538, 1453, 1388, 1267; 1H NMR (300 MHZ, DMSO-d6) δ 11.02 (s, 1H), 8.00-8.12 (m, 2H), 7.40-7.50 (m, 1H), 7.20-7.39 (m, 5H), 4.97 (t, 1H), 3.20 (d, 2H); MS (FD) m/e 357(M+); UV (EtOH) 265 nm (ε=15680), 223 nm (ε=19505), 201 nm (ε=23665). Anal. Calcd for C17H12FN3OS2 : C, 57.13; H,3.38; N,11.76. Found: C,56.89; H, 3.43; N, 11.60.

Provenance & Evidence