Methyl 3-phenyl-DL-alaninate hydrochloride → N-[(2-benzothiazolylamino)thioxomethyl]-DL-phenylalanine methyl ester

Participants

Reaction Steps

A solution of 1-[(2-benzothiazolyl) thiocarbamoyl] imidazole (1.30 g, 5.0 mmol) and DL-phenylalanine methyl ester hydrochloride (1.08 g, 5.0 mmol) in N,N-dimethylformamide (50 mL) was heated at 90° C. for 3 h. The reaction was cooled to room temperature, solvent removed under reduced pressure, recrystallized from ethyl ether-hexanes to provide 1.31 g (70%) of the titled product: mp 168°-169° C.; IR (KBr, cm-1) 3168, 3030, 1732, 1548, 1525, 1206, 1193; 1H NMR (300 MHz, DMSO-d6) δ 10.30 (br s, 1H), 7.88 (d, 1H), 7.62 (d, 1H), 7.32 (t, 1H), 7.20-7.29 (m, 6H), 5.18 (q, 1H), 3.70 (s, 3H), 3.22 (m, 2H); MS (FD) m/e 371 (M+); UV (EtOH) 303 nm (ε=25329), 247 nm (ε=12095), 203 nm (ε=28990). Anal. Calcd for C18H17N3O2S2 : C, 58.20; H, 4.61; N, 11.31. Found: C, 58.19; H, 4.70; N, 11.30.

Provenance & Evidence