(5-AMINO-[1,3,4]THIADIAZOL-2-YLSULFANYL)-ACETIC ACID synthesis

Yield:32418-26-1 75%

Reaction Conditions:

with sodium hydroxide in water at 60; for 4 h;

Steps:

Synthesis of 4, 5 and 6a-k

The mixture of 2-amino-5-mercapto-1,3,4-thiadiazole 4 (5.33 g,0.04 mol), chloroacetic acid (3.78 g, 0.04 mol) and NaOH (3.2 g,0.08 mol) in 50 mL water was heated at 60 C for 4 h. After coolingto room temperature, the solution was neutralized with hydrochloric acid. The precipitate was filtered and then recrystallized from aqueous ethanol (5:1) to obtain purified 5 as pale yellow crystalline solid. Yield 75%, mp 238.4-239.1 C; 1H NMR (400 MHz,DMSO-d6): d 12.82 (s, 1H, COOH), 7.28 (s, 2H, NH2), 3.90 (s, 2H,CH2) ppm; MS (EI): m/z 191.1 [M+] (28), 147.0 (44), 133.1 (100),114.0 (38), 74.1 (19).

References:

Liu, Pingping;Shu, Chen;Liu, Lujie;Huang, Qingchun;Peng, Yanqing [Bioorganic and Medicinal Chemistry,2016,vol. 24,# 8,p. 1866 - 1871]