p-Toluenesulfonic acid monohydrate → HCID 19704095, compound

Participants

Reaction Steps

A solution of N-[[(4-cyano-2-thiazolyl)amino]thioxomethyl]-DL-phenylalanine methyl ester (1.42 g, 4.10 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 24 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 170.1 mg (10%) of the titled product: mp 214°-216° C.; IR (KBr, cm-1) 3294, 3092, 2246, 1781, 1505, 1381, 1325, 1244; 1H NMR (300 MHz, DMSO-d6) δ 11.08 (s, 1H), 8.90 (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 314(M+); UV (EtOH) 259 nm (ε=15097), 205 nm (ε=26419). Anal. Calcd for C14H10N4OS2 : C, 53.49; H, 3.21; N,17.82. Found: C, 53.75; H, 3.43; N, 17.62.

Provenance & Evidence